Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them

ABSTRACT

Phenylacetic acid derivatives of the formula I                    
     where the substituents and the index have the following meanings: 
     X is oxygen or sulfur; 
     R is hydrogen or alkyl; 
     R 1  is hydrogen or alkyl; 
     R 2  is cyano, nitro, trifluoromethyl, halogen, alkyl or alkoxy; 
     m is  0, 1  or  2,  it being possible for the R 2  radicals to be different if m is  2;    
     R 3  is hydrogen, cyano, nitro, hydroxyl, amino, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino or dialkylamino; 
     R 4  is hydrogen, cyano, nitro, hydroxyl, amino, halogen, 
     unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkynyl, alkynyloxy, alkynylthio, alkynylamino, N-alkynyl-N-alkylamino; 
     unsubstituted or substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetaryl amino, N-hetaryl-N-alkylamino; 
     R 5  is hydrogen, 
     unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl or alkylsulfonyl; 
     unsubstituted or substituted aryl, arylcarbonyl, arylsulfonyl; hetaryl, hetarylcarbonyl or hetarylsulfonyl, 
     and their salts, processes and intermediates for their preparation, and their use are described.

This is a Divisional Application of application Ser. No. 09/334,385, filed Jun. 16, 1999 (now U.S. Pat. No. 6,100,263), which is a Divisional Application of application Ser. No. 09/015,692, filed Jan. 29, 1998 (now U.S. Pat. No. 5,981,581), which is a Divisional Application of application Ser. No. 08/687,480, filed on Aug. 5, 1996 (now U.S. Pat. No. 5,889,059), which was filed under 35 U.S.C. 371 as a National Stage application of International Application No. PCT/EP 95/00,007, filed on Jan. 3, 1995.

The present invention relates to phenylacetic acid derivatives of the formula I

where the substituents and the index have the following meanings:

X is oxygen or sulfur;

R is hydrogen and or C₁-C₄-alkyl;

R¹ is hydrogen and or C₁-C₄-alkyl;

R² is cyano, nitro, trifluoromethyl, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;

m is 0, 1 or 2, it being possible for the R² radicals to be different if m is 2;

R³ is hydrogen, cyano, nitro, hydroxyl, amino, halogen,

C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino or di-C₁-C₄-alkylamino;

R⁴ is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkenylamino, N-C₂-C₆-alkenyl-N-C₁-C₆-alkylamino, C₂-C₆-alkynyl, C₂-C₆-alkynyloxy, C₂-C₆-alkynylthio, C₂-C₆-alkynylamino, N-C₂-C₆-alkynyl-N-C₁-C₆-alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonlyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C₁-C₄-alkoxy, arylthio, aryl-C₁-C₄-alkylthio, hetaryl, hetaryloxy, hetaryl-C₁-C₄-alkoxy, hetarylthio, hetaryl-C₁-C₄-alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR⁶)—A_(n)—R⁷;

C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino, N-C₃-C₆-cycloalkyl-N-C₁-C₆-alkylamino, C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkenyloxy, C₃-C₆-cycloalkenylthio, C₃-C₆-cycloalkenylamino, N-C₃-C₆-cycloalkenyl-N-C₁-C₆-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-C₁-C₆-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-C₁-C₆-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-C₁-C₆-alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;

R⁵ is hydrogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di -C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₅-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkyl amino, C₁-C₆-alkyl aminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR⁶)—A_(n)—R⁷;

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR⁶)—A_(n)—R⁷;

where

A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C₁-C₆-alkyl;

n is 0 or 1;

R⁶ is hydrogen or C₁-C₆-alkyl and

R⁷ is hydrogen or C₁-C₆-alkyl,

and their salts.

The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.

Phenylacetic acid derivatives for pest control are disclosed in the literature (EP-A 398 692, EP-A 477 631, EP-A 513 580, EP-A 567 828, EP-A 528 682, EP-A 463 488, WO-A 92113,830).

It is an object of the present invention to provide novel compounds having improved action.

We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use within this context.

The compounds I are obtainable in various ways by processes known per se in the literature.

Fundamentally, it is insignificant in the synthesis of the compounds I whether the group ^(⊖)C(NOCH₃)—CONRR¹ or the group —CH₂ON═C(R³)—C(R⁴)NOR⁵ is constructed first.

The construction of the group —C(NOCH₃)—CONRR¹ is disclosed, for example, in the literature cited at the outset.

The manner of the synthesis of the —CH₂ON—C(R³)═C(R⁴)—NOR³ side chain essentially depends on the nature of the substituents R³ and R⁴.

1. In the case in which R³ and R⁴ are not halogen, the construction of the group —CH₂ON═C(R³)—C(R⁴)—NOR⁵ in general proceeds by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.

L¹ in the formula II is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 370 ff and Houben-Weyl, Vol. 10/1, p. 1189 ff.

The hydroxyimine III required is obtained, for example, by reaction of a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI

L² in the formula VI is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff: Houben-Weyl, Vol. E5, p. 760 ff.

1.1 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyl oxime of the formula V using the dihydroxyimine IV, V then being reacted with the nucleophilically substituted reagent VI to give I.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. 10/1, p. 1189 ff; Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff; Houben-Weyl, Vol. E5, P. 780 ff.

1.2 In a similar manner, it is also possible to prepare the required hydroxyimine of the formula III from a carbonyl-hydroxyimine VII by reaction with a hydroxylamine IXa or its salt IXb.

Q^(⊖) in the formula IXb is the anion of an acid, in particular of an inorganic acid, eg. halide such as chloride.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580; Houben-Weyl, Volume 10/4, p. 73 ff; Houben-Weyl, Vol. E14b, p. 369 ff and p. 385 ff.

1.3 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzylketoxyimine of the formula VIII using the carbonylhydroxyimine VII, VIII then being reacted with the hydroxylamine IXa or its salt IXb to give I.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in Houben-Weyl, Vol. E14b, p. 369 ff; Houben-Weyl, Vol. 10/1, p. 1189 ff and Houben-Weyl, Vol. 10/4, p. 73 ff or EP-A 513 580.

1.4 Another possibility for preparing the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to the benzylhydroxylamine IIa and the further reaction of IIa with a carbonyl compound X.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488 and German Appl. No. 42 28 867.3.

The carbonyl compound X required is obtained, for example, by reaction of a corresponding hydroxyiminocarbonyl VIIa with a nucleophilically substituted reagent VI

or by reaction of a corresponding dicarbonyl XI with a hydroxylamine IXa or its salt IXb

The reactions are carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55 ff, p. 73 ff, p. 180 ff and p. 217 ff, Houben-Weyl, Vol. E14b, p. 307 ff and 369 ff, Houben-Weyl, Vol. E5, p. 780 ff.

1.5 Correspondingly, the compounds I can also be obtained by converting the benzylhydroxylamine IIa first to the corresponding benzyloxyimine of the formula V using the hydroxyiminocarbonyl VIIa, V then being reacted with the nucleophilically substituted reagent VI to give I as described above.

1.6 In a similar manner, the compounds I can also be prepared by converting the benzylhydroxylamine IIa first to the benzyloxyimine VIII using the dicarbonyl of the formula XI and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.

2. Compounds in which R³ and/or R⁴ are a halogen atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 631; J. Org. Chem. 36 (1971), 233; J. Org. Chem. 57 (1992), 3245). Preferably, the corresponding reactions to give the halogen derivative are performed in stages I and VIII.

3. Compounds in which R³ and/or R⁴ are bonded to the structure via an O, S or N atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a halogen atom (cf. Houben-Weyl, Vol. E5, p. 826 ff and 1280 ff, J. Org. Chem. 36 (1971), 233, J. Org. Chem. 46 (1981), 3623). Preferably, the corresponding conversions of the halogen derivative are performed in stages I and VIII.

4. Compounds in which R³ and/or R⁴ are bonded to the structure via an oxygen atom are in some cases also obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 826-829, Aust. J. Chem. 27 (1974), 1341-9). Preferably, the corresponding reactions to give the alkoxy derivatives are performed in stages I and VIII.

5. Compounds in which R³ is not halogen are preferably obtained by first converting a compound X to the corresponding benzoic acid XIII according to the methods described in EP-A 493 711 using a lactone XII and converting XIII via the corresponding halides to the cyanocarbqxylic acids XIV, which are then converted by way of the Pinner reaction (Angew. Chem. 94 (1982), 1) to the α-keto esters XV. The corresponding carboxamides, which are subsequently converted to the compounds I, are obtained from the derivatives XV by amidation.

6. The compounds XVI in which R is hydrogen can also be obtained directly from the carbonyl halides by reaction with isocyanates and subsequent hydrolysis by modifying the process described in 5. (EP 547 825).

7. In another variant, compounds XVI are obtained by converting an ortho halogen compound, after metallation with oxalyl chloride, to the corresponding keto acid chloride, which is subsequently converted with an amine to the corresponding amide XVI (cf. J. Org. Chem. 46 (1981), 46, 212 ff; DE-A 40 42 280; Houben-Weyl, Vol. E5, p. 972 ff).

8. In another variant, the compounds I in which X is oxygen are obtained, starting from the keto esters XV, by first converting the keto function to the oxime ether and converting the oxime ether thus obtained to I using an appropriate amine (Houben-Weyl, Vol. E5, p. 941 ff).

9. The compounds I in which X is sulfur are obtained from the corresponding amides I by reaction with a sulfurizing reagent (eg. phosphorus sulfide or Zawesson's reagent; cf. Houben-Weyl, Vol. IX, 764 ff).

The compounds II are known (EP-A 477 631, EP-A 463 488) or can be prepared by the methods described there.

On account of their C═C and C═N double bonds, the compounds I can be obtained during preparation as E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, eg. by crystallization or chromatography.

If isomer mixtures are obtained during the synthesis, in general, however, a separation is not absolutely necessary, as the individual isomers can in some cases be converted to one another during preparation for application or during application (eg. under the action of light, acid or base). Corresponding conversions can also take place after application, for example during the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.

With reference to the C═NOCH₃ double bond, the cis isomers of the compounds I are preferred with respect to their activity (configuration based on the —OCH₃ group in relation to the —CXNRR¹ group).

With reference to the —C(R³)═NOCH₂— double bond, the Z isomers of the compounds I are preferred with respect to their activity (configuration based on the radical R³ in relation to the —OCH₂— group).

In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, eg. C₁-C₆-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;

dialkylamino: an amino group which carries two straight-chain or branched alkyl groups which are independent of one another and each have 1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms, which are bonded to the structure via a carbonyl group (—CO—);

alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms, which are bonded to the structure via a sulfonyl group (—S(═O)₂—);

alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via a sulfoxyl group (—S(═O)—);

alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group (—CO—);

dialkylaminocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a carbonyl group (—CO—);

alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a thiocarbonyl group (—CS—);

dialkylaminothiocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a thiocarbonyl group (—CS—);

haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, eg. C₁-C₂-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (—O—), eg. C₁-C₆-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

alkoxyzarbonyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via an oxycarbonyl group (—OC(═O)—);

haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, and these groups being bonded to the structure via an oxygen atom;

alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (—S—), eg. C₁-C₆-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;

cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl; straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any desired position, eg. C₂-C₆-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure via an oxygen atom (—O—);

alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to 10 carbon atoms and a double bond in any desired position, which are bonded to the structure via a carbonyl group (—CO—);

alkenylthio or alkenylamino: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure (alkenylthio) via a sulfur atom or (alkenylamino) a nitrogen atom;

alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any desired position, eg. C₂-C₆-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynylcarbonyl: straight-chain or branched alkynyl groups having 3 to 10 carbon atoms and a triple bond in any desired position, which are bonded to the structure via a carbonyl group (—CO—);

alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any desired position, which are bonded to the structure (alkynyloxy) via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom;

cycloalkenyl or cycloalkenyloxy, cycloalkenylthio and cycloalkylamino [sic]: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure directly or (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) a sulfur atom or (cycloalkenylamino) via a nitrogen atom, eg. cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl;

cycloalkoxy or cycloalkylthio and cycloalkylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure (cycloalkoxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino: three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as eg. 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl [sic], 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrizolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl;

aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure directly or (aryloxy) via an oxygen atom (—O—) or (arylthio) a sulfur atom (—S—), (arylcarbonyl) via a carbonyl group (—CO—) or (arylsulfonyl) via a sulfonyl group (—SO₂—), eg. phenyl, naphthyl and phenanthrenyl or phenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;

arylamino: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure via a nitrogen atom;

hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, additionally can contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure directly or (hetaryloxy) via an oxygen atom (—O—) or (hetarylthio) a sulfur atom (—S—), (hetarylcarbonyl) via a carbonyl group (—CO—) or (hetarylsulfonyl) via a sulfonyl group (—SO—), eg.

5-membered heteroaryl, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroarylo containing one to three nitrogen atoms or one nitrogen atom and/or an oxygen or sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the structure via one of the nitrogen ring members;

6-membered heteroaryl, containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazinyl;

benzo-fused 6-membered heteroaryl, containing one to four nitrogen atoms: 6-membered ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene- 1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline,

or the corresponding oxy, thio, carbonyl or sulfonyl groups;

hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure via a nitrogen atom.

The statement partly or completely halogenated is intended to express that in the groups characterized in this way the hydrogen atoms can be partly or completely replaced by identical or different halogen atoms as mentioned above.

With respect to their biological action, compounds of the formula I are preferred in which m is 0.

Equally preferred are compounds of the formula I in which R is hydrogen or methyl.

Equally preferred are compounds of the formula I in which R¹ is hydrogen or methyl.

Compounds of the formula I are particularly preferred in which R is hydrogen and R¹ is hydrogen or methyl.

Compounds of the formula I are particularly preferred in which R and R¹ are simultaneously hydrogen or methyl.

In addition, compounds I are preferred in which R³ is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, methoxy, methylthio or phenyl.

Compounds I are additionally preferred in which R³ is methyl.

In addition, compounds I are preferred in which R³ is methoxy.

Compounds I are additionally preferred in which R³ is hydroxyl.

In addition, compounds I are preferred in which R³ is chlorine.

In addition, compounds I are preferred in which R⁴ is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, isopropyl, methoxy or methylthio.

Compounds I are additionally preferred in which R⁴ is methyl.

In addition, compounds I are preferred in which R⁴ is methoxy.

Compounds I are additionally preferred in which R⁴ is hydroxyl.

In addition, compounds I are preferred in which R⁴ is ethyl.

Compounds I are additionally preferred in which R⁴ is isopropyl.

Compounds I are additionally preferred in which R⁴ is cyclopropyl.

In addition, compounds I are preferred in which R⁴ is unsubstituted or substituted aryl or hetaryl.

In addition, compounds I are preferred in which R⁴ is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.

In addition, compounds I are preferred in which R⁴ is unsubstituted or substituted furyl, thienyl or pyrrolyl.

In addition, compounds I are preferred in which R⁴ is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

In addition, compounds I are preferred in which R⁴ is unsubstituted or substituted oxdiazolyl, thiadiazolyl or triazolyl.

Compounds I are additionally preferred in which R⁴ is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl or di-C₁-C₄-alkylaminocarbonyl.

Compounds I are additionally preferred in which R⁵ is hydrogen, C₁-C₆-alkyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.

In addition, compounds I are preferred in which R⁵ is C₁-C₆-alkyl.

Compounds I are additionally preferred in which R⁵ is methyl or ethyl.

In addition, compounds I are preferred in which R⁵ is arylalkyl or hetarylalkyl.

Compounds I are additionally preferred in which R⁵ is aryloxyalkyl or hetaryloxyalkyl.

Compounds I are additionally preferred in which R⁵ is aryl or hetaryl.

In addition, compounds of the formula I are preferred in which X is O.

In addition, compounds of the formula I are preferred in which X is S.

The compounds I compiled in the following tables are particularly preferred with respect to their use.

Table 1

Compounds of the general formula I.1 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A

Table 2

Compounds of the general formula I.1 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 3

Compounds of the general formula I.2 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 4

Compounds of the general formula I.2 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 5

Compounds of the general formula 1.3 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 6

Compounds of the general formula I.3 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 7

Compounds of the general formula I.4 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 8

Compounds of the general formula I.4 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 9

Compounds of the general formula I.5 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 10

Compounds of the general formula I.5 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 11

Compounds of the general formula I.6 in which (R²)_(m) is hydrogen and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

Table 12

Compounds of the general formula I.6 in which (R²)_(m) is chlorine and the combination of the substituents R³, R⁴ and R⁵ for a compound in each case corresponds to one line of Table A.

TABLE A No. R³ R⁴ R⁵ 1 CH₃ CH₃ H 2 CH₃ CH₃ CH₃ 3 CH₃ CH₃ C₂H₅ 4 CH₃ CH₃ n-C₃H₇ 5 CH₃ CH₃ i-C₃H₇ 6 CH₃ CH₃ Cyclopropyl 7 CH₃ CH₃ n-C₄H₉ 8 CH₃ CH₃ s-C₄H₉ 9 CH₃ CH₃ i-C₄H₉ 10 CH₃ CH₃ t-C₄H₉ 11 CH₃ CH₃ n-C₅H₁₁ 12 CH₃ CH₃ i-C₅H₁₁ 13 CH₃ CH₃ neo-C₅H₁₁ 14 CH₃ CH₃ Cyclopentyl 15 CH₃ CH₃ n-C₆H₁₃ 16 CH₃ CH₃ Cyclohexyl 17 CH₃ CH₃ n-C₉H₁₇ 18 CH₃ CH₃ CH₂CH₂Cl 19 CH₃ CH₃ (CH₂)₄Cl 20 CH₃ CH₃ CH₂CN 21 CH₃ CH₃ CH₂CH₂CN 22 CH₃ CH₃ (CH₂)₃CN 23 CH₃ CH₃ (CH₂)₄CN 24 CH₃ CH₃ (CH₂)₆CN 25 CH₃ CH₃ Cyclohexylmethyl 26 CH₃ CH₃ 2-Cyclohexyleth-1-yl 27 CH₃ CH₃ Cyclopropylmethyl 28 CH₃ CH₃ 2-Cyclopropyleth-1-yl 29 CH₃ CH₃ 2-Methoxyeth-1-yl 30 CH₃ CH₃ 2-Ethoxyeth-1-yl 31 CH₃ CH₃ 2-Isopropoxyeth-1-yl 32 CH₃ CH₃ 3-Methoxyprop-1-yl 33 CH₃ CH₃ 3-Ethoxyprop-1-yl 34 CH₃ CH₃ 3-Isopropoxyprop-1-yl 35 CH₃ CH₃ 4-Methoxybut-1-yl 36 CH₃ CH₃ 4-Isopropoxybut-1-yl 37 CH₃ CH₃ Propen-3-yl 38 CH₃ CH₃ But-2-en-1-yl 39 CH₃ CH₃ 3-Methylbut-2-en-1-yl 40 CH₃ CH₃ 2-Vinyloxyeth-1-yl 41 CH₃ CH₃ Allyloxyeth-1-yl 42 CH₃ CH₃ 2-Trifluoromethoxyeth-1-yl 43 CH₃ CH₃ 3-Trifluoromethoxyprop-1-yl 44 CH₃ CH₃ 4-Difluoromethoxybut-1-yl 45 CH₃ CH₃ Hydroxycarbonylmethyl 46 CH₃ CH₃ Methoxycarbonylmethyl 47 CH₃ CH₃ Aminocarbonylmethyl 48 CH₃ CH₃ N-Methylaminocarbonylmethyl 49 CH₃ CH₃ N,N-Dimethylaminocarbonyl- methyl 50 CH₃ CH₃ 2-Hydroxycarbonyleth-1-yl 51 CH₃ CH₃ 2-Methoxycarbonyleth-1-yl 52 CH₃ CH₃ 2-Aminocarbonyleth-1-yl 53 CH₃ CH₃ 2-N-Methylaminocarbonyleth-1-yl 54 CH₃ CH₃ 2-Dimethylaminocarbonyleth-1-yl 55 CH₃ CH₃ 2-Aminoeth-1-yl 56 CH₃ CH₃ 2-Aminoprop-1-yl 57 CH₃ CH₃ 4-Aminobut-1-yl 58 CH₃ CH₃ 3-Dimethylaminoprop-1-yl 59 CH₃ CH₃ 4-Aminothiocarbonylbut-1-yl 60 CH₃ CH₃ 2-Oxopropyl 61 CH₃ CH₃ Cyclohexyl 62 CH₃ CH₃ Cyclopropyl 63 CH₃ CH₃ Cyclopentyl 64 CH₃ CH₃ 2-Methoxyiminoprop-1-yl 65 CH₃ CH₃ 2-Methoxyiminoeth-1-yl 66 CH₃ CH₃ 6-Aminocarbonylhex-1-yl 67 CH₃ CH₃ 3-Aminothiocarbonylprop-1-yl 68 CH₃ CH₃ 2-Aminothiocarbonyleth-1-yl 69 CH₃ CH₃ Aminothiocarbonylmethyl 70 CH₃ CH₃ 4-(N,N-Dimethylamino)but-1-yl 71 CH₃ CH₃ 2-(Methylthio)eth-1-yl 72 CH₃ CH₃ 2-(Methylsulfonyl)eth-1-yl 73 CH₃ CH₃ 4-(Methylthio)prop-1-yl 74 CH₃ CH₃ 4-(Methylsulfonyl)prop-1-yl 75 CH₃ CH₃ Benyzl 76 CH₃ CH₃ 2-F—C₆H₄—CH₂ 77 CH₃ CH₃ 3-F—C₆H₄—CH₂ 78 CH₃ CH₃ 4-F—C₆H₄—CH₂ 79 CH₃ CH₃ 2,3-F₂—C₆H₃—CH₂ 80 CH₃ CH₃ 2,4-F₂—C₆H₃—CH₂ 81 CH₃ CH₃ 2,5-F₂—C₆H₃—CH₂ 82 CH₃ CH₃ 2,6-F₂—C₆H₃—CH₂ 83 CH₃ CH₃ 3,4-F₂—C₆H₃—CH₂ 84 CH₃ CH₃ 3,5-F₂—C₆H₃—CH₂ 85 CH₃ CH₃ 2-Cl—C₆H₄—CH₂ 86 CH₃ CH₃ 3-Cl—C₆H₄—CH₂ 87 CH₃ CH₃ 4-Cl—C₆H₄—CH₂ 88 CH₃ CH₃ 2,3-Cl₂—C₆H₃—CH₂ 89 CH₃ CH₃ 2,4-Cl₂—C₆H₃—CH₂ 90 CH₃ CH₃ 2,5-Cl₂—C₆H₃—CH₂ 91 CH₃ CH₃ 2,6-Cl₂—C₆H₃—CH₂ 92 CH₃ CH₃ 3,4-Cl₂—C₆H₃—CH₂ 93 CH₃ CH₃ 3,5-Cl₂—C₆H₃—CH₂ 94 CH₃ CH₃ 2,3,4-Cl₃—C₆H₂—CH₂ 95 CH₃ CH₃ 2,3,5-Cl₃—C₆H₂—CH₂ 96 CH₃ CH₃ 2,3,6-Cl₃—C₆H₂—CH₂ 97 CH₃ CH₃ 2,4,5-Cl₃—C₆H₂—CH₂ 98 CH₃ CH₃ 2,4,6-Cl₃—C₆H₂—CH₂ 99 CH₃ CH₃ 3,4,5-Cl₃—C₆H₂—CH₂ 100 CH₃ CH₃ 2-Br—C₆H₄—CH₂ 101 CH₃ CH₃ 3-Br—C₆H₄—CH₂ 102 CH₃ CH₃ 4-Br—C₆H₄—CH₂ 103 CH₃ CH₃ 2,3-Br₂—C₆H₃—CH₂ 104 CH₃ CH₃ 2,4-Br₂—C₆H₃—CH₂ 105 CH₃ CH₃ 2,5-Br₂—C₆H₃—CH₂ 106 CH₃ CH₃ 2,6-Br₂—C₆H₃—CH₂ 107 CH₃ CH₃ 3,4-Br₂—C₆H₃—CH₂ 108 CH₃ CH₃ 3,5-Br₂—C₆H₃—CH₂ 109 CH₃ CH₃ 2-F, 3-Cl—C₆H₃—CH₂ 110 CH₃ CH₃ 2-F, 4-Cl—C₆H₃—CH₂ 111 CH₃ CH₃ 2-F, 5-Cl—C₆H₃—CH₂ 112 CH₃ CH₃ 2-F, 3-Br—C₆H₃—CH₂ 113 CH₃ CH₃ 2-F, 4-Br—C₆H₃—CH₂ 114 CH₃ CH₃ 2-F, 5-Br—C₆H₃—CH₂ 115 CH₃ CH₃ 2-Cl, 3-Br—C₆H₃—CH₂ 116 CH₃ CH₃ 2-Cl, 4-Br—C₆H₃—CH₂ 117 CH₃ CH₃ 2-Cl, 5-Br—C₆H₃—CH₂ 118 CH₃ CH₃ 3-F, 4-Cl—C₆H₃—CH₂ 119 CH₃ CH₃ 3-F, 5-Cl—C₆H₃—CH₂ 120 CH₃ CH₃ 3-F, 6-Cl—C₆H₃—CH₂ 121 CH₃ CH₃ 3-F, 4-Br—C₆H₃—CH₂ 122 CH₃ CH₃ 3-F, 5-Br—C₆H₃—CH₂ 123 CH₃ CH₃ 3-F, 6-Br—C₆H₃—CH₂ 124 CH₃ CH₃ 3-Cl, 4-Br—C₆H₃—CH₂ 125 CH₃ CH₃ 3-Cl, 5-Br—C₆H₃—CH₂ 126 CH₃ CH₃ 3-Cl, 6-Br—C₆H₃—CH₂ 127 CH₃ CH₃ 4-F, 5-Cl—C₆H₃—CH₂ 128 CH₃ CH₃ 4-F, 6-Cl—C₆H₃—CH₂ 129 CH₃ CH₃ 4-F, 5-Br—C₆H₃—CH₂ 130 CH₃ CH₃ 4-F, 6-Br—C₆H₃—CH₂ 131 CH₃ CH₃ 4-Cl, 5-Br—C₆H₃—CH₂ 132 CH₃ CH₃ 5-F, 6-Cl—C₆H₃—CH₂ 133 CH₃ CH₃ 5-F, 6-Br—C₆H₃—CH₂ 134 CH₃ CH₃ 5-Cl, 6-Br—C₆H₃—CH₂ 135 CH₃ CH₃ 3-Br, 4-Cl, 5-Br—C₆H₂—CH₂ 136 CH₃ CH₃ 2-CN—C₆H₄—CH₂ 137 CH₃ CH₃ 3-CN—C₆H₄—CH₂ 138 CH₃ CH₃ 4-CN—C₆H₄—CH₂ 139 CH₃ CH₃ 2-NO₂—C₆H₄—CH₂ 140 CH₃ CH₃ 3-NO₂—C₆H₄—CH₂ 141 CH₃ CH₃ 4-NO₂—C₆H₄—CH₂ 142 CH₃ CH₃ 2-CH₃—C₆H₄—CH₂ 143 CH₃ CH₃ 3-CH₃—C₆H₄—CH₂ 144 CH₃ CH₃ 4-CH₃—C₆H₄—CH₂ 145 CH₃ CH₃ 2,3-(CH₃)₂—C₆H₃—CH₂ 146 CH₃ CH₃ 2,4-(CH₃)₂—C₆H₃—CH₂ 147 CH₃ CH₃ 2,5-(CH₃)₂—C₆H₃—CH₂ 148 CH₃ CH₃ 2,6-(CH₃)₂—C₆H₃—CH₂ 149 CH₃ CH₃ 3,4-(CH₃)₂—C₆H₃—CH₂ 150 CH₃ CH₃ 3,5-(CH₃)₂—C₆H₃—CH₂ 151 CH₃ CH₃ 2-C₂H₅—C₆H₄—CH₂ 152 CH₃ CH₃ 3-C₂H₅—C₆H₄—CH₂ 153 CH₃ CH₃ 4-C₂H₅—C₆H₄—CH₂ 154 CH₃ CH₃ 2-i-C₃H₇—C₆H₄—CH₂ 155 CH₃ CH₃ 3-i-C₃H₇—C₆H₄—CH₂ 156 CH₃ CH₃ 4-i-C₃H₇—C₆H₄—CH₂ 157 CH₃ CH₃ 2-Cyclohexyl-C₆H₄—CH₂ 158 CH₃ CH₃ 3-Cyclohexyl-C₆H₄—CH₂ 159 CH₃ CH₃ 4-Cyclohexyl-C₆H₄—CH₂ 160 CH₃ CH₃ 2-Vinyl-C₆H₄—CH₂ 161 CH₃ CH₃ 3-Vinyl-C₆H₄—CH₂ 162 CH₃ CH₃ 4-Vinyl-C₆H₄—CH₂ 163 CH₃ CH₃ 2-Allyl-C₆H₄—CH₂ 164 CH₃ CH₃ 3-Allyl-C₆H₄—CH₂ 165 CH₃ CH₃ 4-Allyl-C₆H₄—CH₂ 166 CH₃ CH₃ 2-C₆H₅—C₆H₄—CH₂ 167 CH₃ CH₃ 3-C₆H₅—C₆H₄—CH₂ 168 CH₃ CH₃ 4-C₆H₅—C₆H₄—CH₂ 169 CH₃ CH₃ 3-CH₃, 5-t-C₄H₉—C₆H₃—CH₂ 170 CH₃ CH₃ 2-OH—C₆H₄—CH₂ 171 CH₃ CH₃ 3-OH—C₆H₄—CH₂ 172 CH₃ CH₃ 4-OH—C₆H₄—CH₂ 173 CH₃ CH₃ 2-OCH₃—C₆H₄—CH₂ 174 CH₃ CH₃ 3-OCH₃—C₆H₄—CH₂ 175 CH₃ CH₃ 4-OCH₃—C₆H₄—CH₂ 176 CH₃ CH₃ 2,3-(OCH₃)₂—C₆H₃—CH₂ 177 CH₃ CH₃ 2,4-(OCH₃)₂—C₆H₃—CH₂ 178 CH₃ CH₃ 2,5-(OCH₃)₂—C₆H₃—CH₂ 179 CH₃ CH₃ 3,4-(OCH₃)₂—C₆H₃—CH₂ 180 CH₃ CH₃ 3,5-(OCH₃)₂—C₆H₃—CH₂ 181 CH₃ CH₃ 3,4,5-(OCH₃)₃—C₆H₂—CH₂ 182 CH₃ CH₃ 2-OC₂H₅—C₆H₄—CH₂ 183 CH₃ CH₃ 3-OC₂H₅—C₆H₄—CH₂ 184 CH₃ CH₃ 4-OC₂H₅—C₆H₄—CH₂ 185 CH₃ CH₃ 2-O-(n-C₃H₇)—C₆H₄—CH₂ 186 CH₃ CH₃ 3-O-(n-C₃H₇)—C₆H₄—CH₂ 187 CH₃ CH₃ 4-O-(n-C₃H₇)—C₆H₄—CH₂ 188 CH₃ CH₃ 2-O-(i-C₃H₇)—C₆H₄—CH₂ 189 CH₃ CH₃ 3-O-(i-C₃H₇)—C₆H₄—CH₂ 190 CH₃ CH₃ 4-O-(i-C₃H₇)—C₆H₄—CH₂ 191 CH₃ CH₃ 4-O-(n-C₄H₉)—C₆H₄—CH₂ 192 CH₃ CH₃ 3-O-(t-C₄H₉)—C₆H₄—CH₂ 193 CH₃ CH₃ 4-O-(n-C₆H₁₃)—C₆H₄—CH₂ 194 CH₃ CH₃ 2-O-Allyl-C₆H₄—CH₂ 195 CH₃ CH₃ 3-O-Allyl-C₆H₄—CH₂ 196 CH₃ CH₃ 4-0-Allyl-C₆H₄—CH₂ 197 CH₃ CH₃ 2-CF₃—C₆H₄—CH₂ 198 CH₃ CH₃ 3-CF₃—C₆H₄—CH₂ 199 CH₃ CH₃ 4-CF₃—C₆H₄—CH₂ 200 CH₃ CH₃ 2-Acetyl-C₆H₄—CH₂ 201 CH₃ CH₃ 3-Acetyl-C₆H₄—CH₂ 202 CH₃ CH₃ 4-Acetyl-C₆H₄—CH₂ 203 CH₃ CH₃ 2-Methoxycarbonyl-C₆H₄—CH₂ 204 CH₃ CH₃ 3-Methoxycarbonyl-C₆H₄—CH₂ 205 CH₃ CH₃ 4-Methoxycarbonyl-C₆H₄—CH₂ 206 CH₃ CH₃ 2-Aminocarbonyl-C₆H₄—CH₂ 207 CH₃ CH₃ 3-Aminocarbonyl-C₆H₄—CH₂ 208 CH₃ CH₃ 4-Aminocarbonyl-C₆H₄—CH₂ 209 CH₃ CH₃ 2-Dimethylaminocarbo- nyl-C₆H₄—CH₂ 210 CH₃ CH₃ 3-Dimethylaminocarbo- nyl-C₆H₄—CH₂ 211 CH₃ CH₃ 4-Dimethylaminocarbo- nyl-C₆H₄—CH₂ 212 CH₃ CH₃ 2-(N-Methylaminocarbo- nyl)-C₆H₄—CH₂ 213 CH₃ CH₃ 3-(N-Methylaminocarbo- nyl)-C₆H₄—CH₂ 214 CH₃ CH₃ 4-(N-Methylaminocarbo- nyl)-C₆H₄—CH₂ 215 CH₃ CH₃ 2-H₂N—C₆H₄—CH₂ 216 CH₃ CH₃ 3-H₂N—C₆H₄—CH₂ 217 CH₃ CH₃ 4-H₂N—C₆H₄—CH₂ 218 CH₃ CH₃ 2-Aminothiocarbonyl-C₆H₄—CH₂ 219 CH₃ CH₃ 3-Aminothiocarbonyl-C₆H₄—CH₂ 220 CH₃ CH₃ 4-Aminothiocarbonyl-C₆H₄—CH₂ 221 CH₃ CH₃ 2-Methoxyiminomethyl- C₆H₄—CH₂ 222 CH₃ CH₃ 3-Methoxyiminomethyl- C₆H₄—CH₂ 223 CH₃ CH₃ 4-Methoxyiminomethyl- C₆H₄—CH₂ 224 CH₃ CH₃ 2-Formyl-C₆H₄—CH₂ 225 CH₃ CH₃ 3-Formyl-C₆H₄—CH₂ 226 CH₃ CH₃ 4-Formyl-C₆H₄—CH₂ 227 CH₃ CH₃ 2-(1′-Methoxyiminoeth- 1′-yl)-C₆H₄—CH₂ 228 CH₃ CH₃ 3-(1′-Methoxyiminoeth-1′- yl)-C₆H₄—CH₂ 229 CH₃ CH₃ 4-(1′-Methoxyiminoeth-1′- yl)-C₆H₄—CH₂ 230 CH₃ CH₃ 2-SCH₃—C₆H₄—CH₂ 231 CH₃ CH₃ 3-SCH₃—C₆H₄—CH₂ 232 CH₃ CH₃ 4-SCH₃—C₆H₄—CH₂ 233 CH₃ CH₃ 2-SO₂CH₃—C₆H₄—CH₂ 234 CH₃ CH₃ 3-SO₂CH₃—C₆H₄—CH₂ 235 CH₃ CH₃ 4-SO₂CH₃—C₆H₄—CH₂ 236 CH₃ CH₃ 2-OCF₃—C₆H₄—CH₂ 237 CH₃ CH₃ 3-OCF₃—C₆H₄—CH₂ 238 CH₃ CH₃ 4-OCF₃—C₆H₄—CH₂ 239 CH₃ CH₃ 2-OCHF₂—C₆H₄—CH₂ 240 CH₃ CH₃ 3-OCHF₂—C₆H₄—CH₂ 241 CH₃ CH₃ 4-OCHF₂—C₆H₄—CH₂ 242 CH₃ CH₃ 3-CF₃, 4-OCF₃—C₆H₃—CH₂ 243 CH₃ CH₃ 1-Naphthyl-CH₂ 244 CH₃ CH₃ 2-Naphthyl-CH₂ 245 CH₃ CH₃ 2-Phenoxyeth-1-yl 246 CH₃ CH₃ 2-(2′-Chlorophenoxy)eth-1-yl 247 CH₃ CH₃ 2-(3′-Chlorophenoxy)eth-1-yl 248 CH₃ CH₃ 2-(4′-Chlorophenoxy)eth-1-yl 249 CH₃ CH₃ 2-(3′,5′-Dichlorophenoxy)- eth-1-yl 250 CH₃ CH₃ 2-(2′-Cyanophenoxy)eth-1-yl 251 CH₃ CH₃ 2-(3′-Cyanophenoxy)eth-1-yl 252 CH₃ CH₃ 2-(4′-Cyanophenoxy)eth-1-yl 253 CH₃ CH₃ 2-(2′-Methylphenoxy)eth-1-yl 254 CH₃ CH₃ 2-(3′-Methylphenoxy)eth-1-yl 255 CH₃ CH₃ 2-(4′-Methylphenoxy)eth-1-yl 256 CH₃ CH₃ 2-(3′-t-Butylphenoxy)eth-1-yl 257 CH₃ CH₃ 2-(4′-t-Butylphenoxy)eth-1-yl 258 CH₃ CH₃ 2-(2′-Nitrophenoxy)eth-1-yl 259 CH₃ CH₃ 2-(3′-Nitrophenoxy)eth-1-yl 260 CH₃ CH₃ 2-(4′-Nitrophenoxy)eth-1-yl 261 CH₃ CH₃ 2-(2′-Methoxyphenoxy)eth-1-yl 262 CH₃ CH₃ 2-(3′-Methoxyphenoxy)eth-1-yl 263 CH₃ CH₃ 2-(4′-Methoxyphenoxy)eth-1-yl 264 CH₃ CH₃ 2-(2′-Trifluoromethylphen- oxy)eth-1-yl 265 CH₃ CH₃ 2-(3′-Trifluoromethylphen- oxy)eth-1-yl 266 CH₃ CH₃ 2-(4′-Trifluoromethylphen- oxy)eth-1-yl 267 CH₃ CH₃ 2-(2′-Acetylphenoxy)eth-1-yl 268 CH₃ CH₃ 2-(3′-Acetylphenoxy)eth-1-yl 269 CH₃ CH₃ 2-(4′-Acetylphenoxy)eth-1-yl 270 CH₃ CH₃ 2-(2′-Methoxycarbonyl)eth-1-yl 271 CH₃ CH₃ 2-(3′-Methoxycarbonyl)eth-1-yl 272 CH₃ CH₃ 2-(4′-Methoxycarbonyl)eth-1-yl 273 CH₃ CH₃ 2-(2′-Dimethylamino- carbonyl)eth-1-yl 274 CH₃ CH₃ 2-(3′-Dimethylamino- carbonyl)eth-1-yl 275 CH₃ CH₃ 2-(4′-Dimethylamino- carbonyl)eth-1-yl 276 CH₃ CH₃ 2-(2′-Aminothiocarbonyl)eth-1-yl 277 CH₃ CH₃ 2-(3′-Aminothiocarbonyl)eth-1-yl 278 CH₃ CH₃ 2-(4′-Aminothiocarbonyl)eth-1-yl 279 CH₃ CH₃ 2-(2′-Methylsulfonyl)eth-1-yl 280 CH₃ CH₃ 2-(3′-Methylsulfonyl)eth-1-yl 281 CH₃ CH₃ 2-(4′-Methylsulfonyl)eth-1-yl 282 CH₃ CH₃ 3-Phenoxyprop-1-yl 283 CH₃ CH₃ 3-(2′-Chlorophenoxy)prop-1-yl 284 CH₃ CH₃ 3-(3′-Chlorophenoxy)prop-1-yl 285 CH₃ CH₃ 3-(4′-Chlorophenoxy)prop-1-yl 286 CH₃ CH₃ 3-(3′,5′,Dichlorophenoxy)prop-1-yl 287 CH₃ CH₃ 3-(2′-Cyanophenoxy)prop-1-yl 288 CH₃ CH₃ 3-(3′-Cyanophenoxy)prop-1-yl 289 CH₃ CH₃ 3-(4′-Cyanophenoxy)prop-1-yl 290 CH₃ CH₃ 3-(2′-Methylphenoxy)prop-1-yl 291 CH₃ CH₃ 3-(3′-Methylphenoxy)prop-1-yl 292 CH₃ CH₃ 3-(4′-Methylphenoxy)prop-1-yl 293 CH₃ CH₃ 3-(2′-Methoxyphenoxy)prop-1-yl 294 CH₃ CH₃ 3-(3′-Methoxyphenoxy)prop-1-yl 295 CH₃ CH₃ 3-(4′-Methoxyphenoxy)prop-1-yl 296 CH₃ CH₃ 3-(2′-Trifluoromethyl- phenoxy)prop-1-yl 297 CH₃ CH₃ 3-(3′-Trifluoromethyl- phenoxy)prop-1-yl 298 CH₃ CH₃ 3-(4′-Trifluoromethyl- phenoxy)prop-1-yl 299 CH₃ CH₃ 4-Phenoxybut-1-yl 300 CH₃ CH₃ 2-Phenyleth-1-yl 301 CH₃ CH₃ 2-(2′-Chlorophenyl)eth-1-yl 302 CH₃ CH₃ 2-(3′-Chlorophenyl)eth-1-yl 303 CH₃ CH₃ 2-(4′-Chlorophenyl)eth-1-yl 304 CH₃ CH₃ 2-(3′,5′-Dichlorophenyl)eth-1-yl 305 CH₃ CH₃ 2-(2′-Cyanophenyl)eth-1-yl 306 CH₃ CH₃ 2-(3′-Cyanophenyl)eth-1-yl 307 CH₃ CH₃ 2-(4′-Cyanophenyl)eth-1-yl 308 CH₃ CH₃ 2-(2′-Methylphenyl)eth-1-yl 309 CH₃ CH₃ 2-(3′-Methylphenyl)eth-1-yl 310 CH₃ CH₃ 2-(4′-Methylphenyl)eth-1-yl 311 CH₃ CH₃ 2-(2′-Methoxyphenyl)eth-1-yl 312 CH₃ CH₃ 2-(3′-Methoxyphenyl)eth-1-yl 313 CH₃ CH₃ 2-(4′-Methoxyphenyl)eth-1-yl 314 CH₃ CH₃ 2-(2′-Trifluoromethyl- phenyl)eth-1-yl 315 CH₃ CH₃ 2-(3′-Trifluoromethyl- phenyl)eth-1-yl 316 CH₃ CH₃ 2-(4′-Trifluoromethyl- phenyl)eth-1-yl 317 CH₃ CH₃ 3-Phenylprop-1-yl 318 CH₃ CH₃ 3-(2′-Chlorophenyl)prop-1-yl 319 CH₃ CH₃ 3-(3′-Chlorophenyl)prop-1yl 320 CH₃ CH₃ 3-(4′-Chlorophenyl)prop-1-yl 321 CH₃ CH₃ 3-(2′-Cyanophenyl)prop-1-yl 322 CH₃ CH₃ 3-(3′-Cyanophenyl)prop-1-yl 323 CH₃ CH₃ 3-(4′-Cyanophenyl)prop-1-yl 324 CH₃ CH₃ 3-(2′-Trifluoromethyl- phenyl)prop-1-yl 325 CH₃ CH₃ 4-Phenylbut-1-yl 326 CH₃ CH₃ 4-(4′-Chlorophenyl)but-1-yl 327 CH₃ CH₃ 6-(4′-Chlorophenyl)hex-1-yl 328 CH₃ CH₃ 2-Pyridylmethyl 329 CH₃ CH₃ 3-Pyridylmethyl 330 CH₃ CH₃ 4-Pyridylmethyl 331 CH₃ CH₃ 4-Chloropyridin-2-ylmethyl 332 CH₃ CH₃ 5-Chloropyridin-2-ylmethyl 333 CH₃ CH₃ 6-Chloropyridin-2-ylmethyl 334 CH₃ CH₃ 5-Chloropyridin-3-ylmethyl 335 CH₃ CH₃ 6-Chloropyridin-3-ylmethyl 336 CH₃ CH₃ 2-Chloropyridin-4-ylmethyl 337 CH₃ CH₃ 2-Pyrimidinylmethyl 338 CH₃ CH₃ 4-Chloropyrimidin-2-yl-methyl 339 CH₃ CH₃ 5-Chloropyrimidin-2-yl-methyl 340 CH₃ CH₃ 2-Chloropyrimidin-4-yl-methyl 341 CH₃ CH₃ 6-Chloropyrimidin-4-yl-methyl 342 CH₃ CH₃ 2-Chloropyrimidin-5-yl-methyl 343 CH₃ CH₃ 4-Pyridazinylmethyl 344 CH₃ CH₃ 2-Pyrazinylmethyl 345 CH₃ CH₃ 5-Chloropyrazin-2-ylmethyl 346 CH₃ CH₃ 6-Chloropyrazin-2-ylmethyl 347 CH₃ CH₃ 3-Pyridazinylmethyl 348 CH₃ CH₃ 6-Chloropyridazin-3-yl-methyl 349 CH₃ CH₃ 1,3,5-Triazinylmethyl 350 CH₃ CH₃ 2-Furylmethyl 351 CH₃ CH₃ 3-Furylmethyl 352 CH₃ CH₃ 4-Bromofur-2-ylmethyl 353 CH₃ CH₃ 5-Chlorofur-2-ylmethyl 354 CH₃ CH₃ 2-Thienylmethyl 355 CH₃ CH₃ 3-Thienylmethyl 356 CH₃ CH₃ 5-Methylthien-3-ylmethyl 357 CH₃ CH₃ 5-Chlorothien-2-ylmethyl 358 CH₃ CH₃ 2-Chlorothien-4-ylmethyl 359 CH₃ CH₃ 2-Pyrrolylmethyl 360 CH₃ CH₃ 3-Pyrrolylmethyl 361 CH₃ CH₃ 2-Oxazolylmethyl 362 CH₃ CH₃ 4-Methyloxazol-2-ylmethyl 363 CH₃ CH₃ 5-Methyloxazol-2-ylmethyl 364 CH₃ CH₃ 4-Chlorooxazol-2-ylmethyl 365 CH₃ CH₃ 5-Chlorooxazol-2-ylmethyl 366 CH₃ CH₃ 4-Oxazolylmethyl 367 CH₃ CH₃ 2-Methyloxazol-4-ylmethyl 368 CH₃ CH₃ 5-Methyloxazol-4-ylmethyl 369 CH₃ CH₃ 2-Chlorooxazol-4-ylmethyl 370 CH₃ CH₃ 5-Chlorooxazol-4-ylmethyl 371 CH₃ CH₃ 5-Oxazolylmethyl 372 CH₃ CH₃ 2-Methyloxazol-5-ylmethyl 373 CH₃ CH₃ 4-Methyloxazol-5-ylmethyl 374 CH₃ CH₃ 2-Chlorooxazol-5-ylmethyl 375 CH₃ CH₃ 4-Chlorooxazol-5-ylmethyl 376 CH₃ CH₃ 2-Thiazolylmethyl 377 CH₃ CH₃ 4-Methylthiazol-2-ylmethyl 378 CH₃ CH₃ 5-Methylthiazol-2-ylmethyl 379 CH₃ CH₃ 4-Chlorothiazol-2-ylmethyl 380 CH₃ CH₃ 5-Chlorothiazol-2-ylmethyl 381 CH₃ CH₃ 4-Thiazolylmethyl 382 CH₃ CH₃ 2-Methylthiazol-4-ylmethyl 383 CH₃ CH₃ 5-Methylthiazol-4-ylmethyl 384 CH₃ CH₃ 2-Chlorothiazol-4-ylmethyl 385 CH₃ CH₃ 5-Chlorothiazol-4-ylmethyl 386 CH₃ CH₃ 5-Thiazolylmethyl 387 CH₃ CH₃ 2-Methylthiazol-5-ylmethyl 388 CH₃ CH₃ 4-Methylthiazol-5-ylmethyl 389 CH₃ CH₃ 2-Chlorothiazol-5-ylmethyl 390 CH₃ CH₃ 4-Chlorothiazol-5-ylmethyl 391 CH₃ CH₃ 3-Isoxazolylmethyl 392 CH₃ CH₃ 4-Methylisoxazol-3-ylmethyl 393 CH₃ CH₃ 5-Methylisoxazol-3-ylmethyl 394 CH₃ CH₃ 4-Chloroisoxazol-3-ylmethyl 395 CH₃ CH₃ 5-Chloroisoxazol-3-ylmethyl 396 CH₃ CH₃ 4-Isoxazolylmethyl 397 CH₃ CH₃ 3-Methylisoxazol-4-ylmethyl 398 CH₃ CH₃ 5-Methylisoxazol-4-ylmethyl 399 CH₃ CH₃ 3-Chloroisoxazol-4-ylmethyl 400 CH₃ CH₃ 5-Chloroisoxazol-4-ylmethyl 401 CH₃ CH₃ 5-Isoxazolylmethyl 402 CH₃ CH₃ 3-Methylisoxazol-5-ylmethyl 403 CH₃ CH₃ 4-Methylisoxazol-5-ylmethyl 404 CH₃ CH₃ 3-Chloroisoxazol-5-ylmethyl 405 CH₃ CH₃ 4-Chloroisoxazol-5-ylmethyl 406 CH₃ CH₃ 3-Isothiazolylmethyl 407 CH₃ CH₃ 4-Methylisothiazol-3-yl-methyl 408 CH₃ CH₃ 5-Methylisothiazol-3-yl-methyl 409 CH₃ CH₃ 4-Chloroisothiazol-3-yl-methyl 410 CH₃ CH₃ 5-Chloroisothiazol-3-yl-methyl 411 CH₃ CH₃ 4-Isothiazolylmethyl 412 CH₃ CH₃ 3-Methylisothiazol-4-yl-methyl 413 CH₃ CH₃ 5-Methylisothiazol-4-yl-methyl 414 CH₃ CH₃ 3-Chloroisothiazol-4-yl-methyl 415 CH₃ CH₃ 5-Chloroisothiazol-4-yl-methyl 416 CH₃ CH₃ 5-Isothiazolylmethyl 417 CH₃ CH₃ 3-Methylisothiazol-5-yl-methyl 418 CH₃ CH₃ 4-Methylisothiazol-5-yl-methyl 419 CH₃ CH₃ 3-Chloroisothiazol-5-yl-methyl 420 CH₃ CH₃ 4-Chloroisothiazol-5-yl-methyl 421 CH₃ CH₃ 4-Imidazolylmethyl 422 CH₃ CH₃ 1-Phenylpyrazol-3-ylmethyl 423 CH₃ CH₃ 1-Methylimidazol-4-ylmethyl 424 CH₃ CH₃ 1-Phenyl-1,2,4-triazol-3-ylmethyl 425 CH₃ CH₃ 1,2,4-Oxadiazol-3-ylmethyl 426 CH₃ CH₃ 5-Chloro-1,2,4-oxadiazol-3- ylmethyl 427 CH₃ CH₃ 5-Methyl-1,2,4-oxadiazol-3- ylmethyl 428 CH₃ CH₃ 5-Trifluoromethyl-1,2,4- oxadiazol-3-ylmethyl 429 CH₃ CH₃ 1,3,4-Oxadiazol-2-ylmethyl 430 CH₃ CH₃ 5-Chloro-1,3,4-oxadiazol-2- ylmethyl 431 CH₃ CH₃ 5-Methyl-1,3,4-oxadiazol-2- ylmethyl 432 CH₃ CH₃ 5-Methoxy-1,3,4-oxadiazol-2- ylmethyl 433 CH₃ CH₃ 1,2,4-Thiadiazol-3-ylmethyl 434 CH₃ CH₃ 5-Chloro-1,2,4-thiadiazol-3- ylmethyl 435 CH₃ CH₃ 5-Methyl-1,2,4-thiadiazol-3- ylmethyl 436 CH₃ CH₃ 1,3,4-Thiadiazol-2-ylmethyl 437 CH₃ CH₃ 5-Chloro-1,3,4-thiadiazol-2- ylmethyl 438 CH₃ CH₃ 5-Methyl-1,3,4-thiadiazol-2- ylmethyl 439 CH₃ CH₃ 5-Cyano-1,3,4-thiadiazol-2- ylmethyl 440 CH₃ CH₃ 2-(2′-Pyridinyloxy)eth-1-yl 441 CH₃ CH₃ 2-(3′-Pyridinyloxy)eth-1-yl 442 CH₃ CH₃ 2-(4′-Pyridinyloxy)eth-1-yl 443 CH₃ CH₃ 2-(2′-Pyrimidinyloxy)eth-1-yl 444 CH₃ CH₃ 2-(4′-Pyrimidinyloxy)eth-1-yl 445 CH₃ CH₃ 2-(5′-Pyrimidinyloxy)eth-1-yl 446 CH₃ CH₃ 2-(2′-Pyrazinyloxy)eth-1-yl 447 CH₃ CH₃ 2-(2′-Pyridazinyloxy)eth-1-yl 448 CH₃ CH₃ 2-(3′-Pyridazinyloxy)eth-1-yl 449 CH₃ CH₃ 2-(1′,3′,5′-Triazin- yloxy)eth-1-yl 450 CH₃ CH₃ 2-(5′-Methylisoxazol-3′-yl- oxy)eth-1-yl 451 CH₃ CH₃ 2-(5′-Chloroisoxazoi-3′-yl- oxy)eth-1-yl 452 CH₃ CH₃ 2-(2′-Methoxythiazol-4′-yl- oxy)eth-1-yl 453 CH₃ CH₃ 2-(4′-Chlorooxazol-2′-yl- oxy)eth-1-yl 454 CH₃ CH₃ 2-(1′-Phenyl-1′H-1′,2′,4′- triazol-3′-yloxy)eth-1-yl 455 CH₃ CH₃ 2-(1′-Phenylpyrazol-3′-yl- oxy)eth-1-yl 456 CH₃ CH₃ C₆H₅ 457 CH₃ CH₃ 2-Cl—C₆H₄ 458 CH₃ CH₃ 3-Cl—C₆H₄ 459 CH₃ CH₃ 4-Cl—C₆H₄ 460 CH₃ CH₃ 2,3-Cl₂—C₆H₃ 461 CH₃ CH₃ 2,4-Cl₂—C₆H₃ 462 CH₃ CH₃ 2,5-Cl₂—C₆H₃ 463 CH₃ CH₃ 3,4-Cl₂—C₆H₃ 464 CH₃ CH₃ 3,5-Cl₂—C₆H₃ 465 CH₃ CH₃ 4-CN—C₆H₄ 466 CH₃ CH₃ 2-NO₂—C₆H₄ 467 CH₃ CH₃ 3-NO₂—C₆H₄ 468 CH₃ CH₃ 4-NO₂—C₆H₄ 469 CH₃ CH₃ 2,4-(NO₂)₂—C₆H₃ 470 CH₃ CH₃ 2-CH₃—C₆H₄ 471 CH₃ CH₃ 3-CH₃—C₆H₄ 472 CH₃ CH₃ 4-CH₃—C₆H₄ 473 CH₃ CH₃ 2,3-(CH₃)₂—C₆H₃ 474 CH₃ CH₃ 2,4-(CH₃)₂—C₆H₃ 475 CH₃ CH₃ 2,5-(CH₃)₂—C₆H₃ 476 CH₃ CH₃ 2,6-(CH₃)₂—C₆H₃ 477 CH₃ CH₃ 2-C₆H₅—C₆H₄ 478 CH₃ CH₃ 3-C₆H₅—C₆H₄ 479 CH₃ CH₃ 4-C₆H₅—C₆H₄ 480 CH₃ CH₃ 3-OCH₃—C₆H₄ 481 CH₃ CH₃ 4-OCH₃—C₆H₄ 482 CH₃ CH₃ 3-Acetyl-C₆H₄ 483 CH₃ CH₃ 4-Acetyl-C₆H₄ 484 CH₃ CH₃ 3-Methoxycarbonyl-C₆H₄ 485 CH₃ CH₃ 4-Methoxycarbonyl-C₆H₄ 486 CH₃ CH₃ 3-CF₃—C₆H₄ 487 CH₃ CH₃ 4-CF₃—C₆H₄ 488 CH₃ CH₃ 2-Naphthyl 489 CH₃ CH₃ 6-Chloropyridazin-3-yl 490 CH₃ CH₃ 5-Chloropyrazin-2-yl 491 CH₃ CH₃ Quinolin-2-yl 492 CH₃ CH₃ 2,5-Dimethylpyrazin-3-yl 493 CH₃ CH₃ Pyrazin-2-yl 494 CH₃ CH₃ 3-Chloropyrid-2-yl 495 CH₃ CH₃ 6-Chloropyrid-2-yl 496 CH₃ CH₃ 4-Trifluoromethy [sic], 6-Chloropyrid-2-yl 497 CH₃ CH₃ 4-Trifluoromethylpyrid-2-yl 498 CH₃ CH₃ 6-Trifluoromethylpyrid-2-yl 499 CH₃ CH₃ 6-Methoxypyrid-2-yl 500 CH₃ CH₃ 5-Chloropyrid-2-yl 501 CH₃ CH₃ Pyrid-2-yl 502 CH₃ CH₃ Benzothiazol-2-yl 503 CH₃ CH₃ 7-Chloroquinolin-4-yl 504 CH₃ CH₃ 3-Nitropyrid-2-yl 505 CH₃ CH₃ Pyrrol-3-yl 506 CH₃ CH₃ Pyrrol-2-yl 507 CH₃ CH₃ 2,6-Dioctylpyrid-4-yl 508 CH₃ CH₃ 5-Nitropyrid-2-yl 509 CH₃ CH₃ Pyrid-4-yl 510 CH₃ CH₃ Pyrid-3-yl 511 CH₃ CH₃ Pyrimidin-2-yl 512 CH₃ CH₃ Pyrimidin-4-yl 513 CH₃ CH₃ Quinazolin-4-yl 514 CH₃ CH₃ 6-Chloropyrimidin-4-yl 515 CH₃ CH₃ 6-Methoxypyrimidin-4-yl 516 CH₃ CH₃ 2,5,6-Trichloropyrimidin-4-yl 517 CH₃ CH₃ 2,6-Dimethylpyrimidin-4-yl 518 CH₃ CH₃ 2-Methyl, 6-Chloropyrimidin-4-yl 519 CH₃ CH₃ 2-Methyl, 6-Ethoxypyrimidin-4-yl 520 CH₃ CH₃ 4,5,6-Trichloropyrimidin-2-yl 521 CH₃ CH₃ 4,6-Dimethoxypyrimidin-2-yl 522 CH₃ CH₃ 4,6-Dimethylpyrimidin-2-yl 523 CH₃ CH₃ 4,6-Dichloropyrimidin-2-yl 524 CH₃ CH₃ 4-Methyl, 6-methoxypyrimidin-2-yl 525 CH₃ CH₃ 4-Chloro, 6-methoxypyrimidin-2-yl 526 CH₃ CH₃ 6-Chloroquinoxalin-2-yl 527 CH₃ CH₃ 3,6-Dichloro-1,2,4-triazin-5-yl 528 CH₃ CH₃ 4-Methoxy-1,3,5-triazin-2-yl 529 CH₃ CH₃ 4-Ethoxy-1,3,5-triazin-2-yl 530 CH₃ CH₃ 4,6-Dichloro-1,3,5-triazin-2-yl 531 CH₃ CH₃ 4-Ethoxy, 6-Chloro-1,3,5-triazin-2-yl 532 CH₃ CH₃ Isoxazol-3-yl 533 CH₃ CH₃ Thien-2-yl 534 CH₃ CH₃ Fur-2-yl 535 CH₃ CH₃ Thiatriazol-5-yl 536 CH₃ CH₃ (E)-1-Chloropropen-3-yl 537 CH₃ CH₃ (E)-4-(4′-Chlorophenyl)but- 2-en-1-yl 538 CH₃ CH₃ Propyn-3-yl 539 CH₃ CH₃ Methylcarbonyl 540 CH₃ CH₃ Ethylcarbonyl 541 CH₃ CH₃ n-Propylcarbonyl 542 CH₃ CH₃ i-Propylcarbonyl 543 CH₃ CH₃ n-Butylcarbonyl 544 CH₃ CH₃ s-Butylcarbonyl 545 CH₃ CH₃ i-Butylcarbonyl 546 CH₃ CH₃ t-Butylcarbonyl 547 CH₃ CH₃ n-Pentylcarbonyl 548 CH₃ CH₃ i-Pentylcarbonyl 549 CH₃ CH₃ neo-Pentylcarbonyl 550 CH₃ CH₃ n-Hexylcarbonyl 551 CH₃ CH₃ n-Octylcarbonyl 552 CH₃ CH₃ 1-Propenylcarbonyl 553 CH₃ CH₃ 2-Penten-1-yl-carbonyl 554 CH₃ CH₃ 2,5-Heptadien-1-yl-carbonyl 555 CH₃ CH₃ Benzoyl 556 CH₃ CH₃ 2-Chlorobenzoyl 557 CH₃ CH₃ 3-Chlorobenzoyl 558 CH₃ CH₃ 4-Chlorobenzoyl 559 CH₃ CH₃ 2-Cyanobenzoyl 560 CH₃ CH₃ 3-Cyanobenzoyl 561 CH₃ CH₃ 4-Cyanobenzoyl 562 CH₃ CH₃ 4-Methoxybenzoyl 563 CH₃ CH₃ 2-Pyridylcarbonyl 564 CH₃ CH₃ 3-Pyridylcarbonyl 565 CH₃ CH₃ 4-Pyridylcarbonyl 566 CH₃ CH₃ 2-Pyrimidinylcarbonyl 567 CH₃ CH₃ 2-Oxazolylcarbonyl 568 CH₃ CH₃ 4-Methylisoxazol-5-yl-carbonyl 569 CH₃ CH₃ Methylsulfonyl 570 CH₃ CH₃ Ethylsulfonyl 571 CH₃ CH₃ n-Propylsulfonyl 572 CH₃ CH₃ i-Propylsulfonyl 573 CH₃ CH₃ n-Butylsulfonyl 574 CH₃ CH₃ t-Butylsulfonyl 575 CH₃ CH₃ n-Pentylsulfonyl 576 CH₃ CH₃ neo-Pentylsulfonyl 577 CH₃ CH₃ n-Hexylsulfonyl 578 CH₃ CH₃ n-Octylsulfonyl 579 CH₃ CH₃ Phenylsulfonyl 580 CH₃ CH₃ 2-Chlorophenylsulfonyl 581 CH₃ CH₃ 3-Chlorophenylsulfonyl 582 CH₃ CH₃ 4-Chlorophenylsulfonyl 583 CH₃ CH₃ 2-Cyanophenylsulfonyl 584 CH₃ CH₃ 3-Cyanophenylsulfonyl 585 CH₃ CH₃ 4-Cyanophenylsulfonyl 586 CH₃ CH₃ 2-Pyridylsulfonyl 587 CH₃ CH₃ 3-Pyridylsulfonyl 588 CH₃ CH₃ 4-Pyridylsulfonyl 589 CH₃ CH₃ 2-Pyrimidinylsulfonyl 590 CH₃ CH₃ 4-Oxazolylsulfonyl 591 CH₃ CH₃ 5-Chlorothiazol-2-yl-sulfonyl 592 CH₃ CH₃ 2-t-C₄H₉—C₆H₄—CH₂ 593 CH₃ CH₃ 3-t-C₄H₉—C₆H₄—CH₂ 594 CH₃ CH₃ 4-t-C₄H₉—C₆H₄—CH₂ 595 CH₃ CH₃ 2-(4′-Chlorothiazol-2′-yl- oxy)eth-1-yl 596 CH₃ CH₃ 2-(1′-Methylpyrazol-4′-yl- oxy)eth-1-yl 597 CH₃ CH₃ 4-Br—C₆H₄ 598 CH₃ CH₃ 3,5-(CH₃)₂—C₆H₃ 599 CH₃ CH₃ 4-C₂H₅—C₆H₄ 600 CH₃ CH₃ 3-Dimethylaminocarbonyl-C₆H₄ 601 CH₃ CH₃ 4-Dimethylaminocarbonyl-C₆H₄ 602 CH₃ CH₃ 2-Hydroxyprop-1-y1 603 CH₃ CH₃ 6-Hydroxy-2-methyl- pyrimidin-4-ylmethyl 604 CH₃ CH₃ [6-OH,2-CH(CH₃)₂-pyrimidin- 4-yl]-CH₂ 605 CH₃ CH₃ [6-OH,2-CH(CH₂)₂-pyrimidin- 4-yl]-CH₂ 606 CH₃ CH₃ 5-(2′-Furan)-pent-1-yl 607 CH₃ CH₃ 5-(2′-N-Methylpyr- rol)-pent-1-yl 608 CH₃ CH₃ [2-(4-Cl—C₆H₄)-oxazol-4-yl]- CH₂ 609 CH₃ CH₃ 3-CF₃-pyridin-2-yl 610 CH₃ CH₃ 5-CF₃-pyridin-2-yl 611 CH₃ CH₃ 6-(2′-Thienyl)hex-1-yl 612 CH₃ t-C₄H₉ H 613 CH₃ t-C₄H₉ CH₃ 614 CH₃ t-C₄H₉ C₂H₅ 615 CH₃ t-C₄H₉ n-C₃H₇ 616 CH₃ t-C₄H₉ i-C₃H₇ 617 CH₃ t-C₄H₉ Cyclopropyl 618 CH₃ t-C₄H₉ n-C₄H₉ 619 CH₃ t-C₄H₉ t-C₄H₉ 620 CH₃ t-C₄H₉ n-C₆H₁₃ 621 CH₃ t-C₄H₉ (E)-1-Chloropropen-3-yl 622 CH₃ t-C₄H₉ Propyn-3-yl 623 CH₃ t-C₄H₉ 3-Methylbut-2-en-1-yl 624 CH₃ t-C₄H₉ 2-Naphthyl-CH₂ 625 CH₃ t-C₄H₉ 4-Cl—C₆H₄—CH₂ 626 CH₃ t-C₄H₉ (E)-4-(4′-Chlorophenyl)but- 2-en-1-yl 627 CH₃ t-C₄H₉ 6-(4′-Chlorophenyl)hex-1-yl 628 CH₃ t-C₄H₉ 3-CF₃—C₆H₄ 629 CH₃ C₆H₅ H 630 CH₃ C₆H₅ CH₃ 631 CH₃ C₆H₅ C₂H₅ 632 CH₃ C₆H₅ n-C₃H₇ 633 CH₃ C₆H₅ i-C₃H₇ 634 CH₃ C₆H₅ Cyclopropyl 635 CH₃ C₆H₅ n-C₄H₉ 636 CH₃ C₆H₅ t-C₄H₉ 637 CH₃ C₆H₅ n-C₆H₁₃ 638 CH₃ C₆H₅ 4-Cl—C₆H₄—CH₂ 639 CH₃ C₆H₅ 3-CF₃—C₆H₄ 640 CH₃ C₆H₅ 6-(4′-Chlorophenyl)hex-1-yl 641 CH₃ C₆H₅ (E)-4-(4′-Chlorophenyl)but- 2-en-1-yl 642 CH₃ H H 643 CH₃ H CH₃ 644 CH₃ H C₂H₅ 645 CH₃ H n-C₃H₇ 646 CH₃ H i-C₃H₇ 647 CH₃ OH H 648 CH₃ OH CH₃ 649 CH₃ OH C₂H₅ 650 CH₃ OH n-C₃H₇ 651 CH₃ OH i-C₃H₇ 652 CH₃ Cl CH₃ 653 CH₃ Cl C₂H₅ 654 CH₃ Cl n-C₃H₇ 655 CH₃ Cl i-C₃H₇ 656 CH₃ OCH₃ H 657 CH₃ OCH₃ CH₃ 658 CH₃ OCH₃ C₂H₅ 659 CH₃ OCH₃ n-C₃H₇ 660 CH₃ OCH₃ i-C₃H₇ 661 CH₃ SCH₃ H 662 CH₃ SCH₃ CH₃ 663 CH₃ SCH₃ C₂H₅ 664 CH₃ SCH₃ n-C₃H₇ 665 CH₃ SCH₃ i-C₃H₇ 666 CH₃ Cyclopropyl H 667 CH₃ Cyclopropyl CH₃ 668 CH₃ Cyclopropyl C₂H₅ 669 CH₃ Cyclopropyl n-C₃H₇ 670 CH₃ Cyclopropyl i-C₃H₇ 671 CH₃ 2-Pyridyl H 672 CH₃ 2-Pyridyl CH₃ 673 CH₃ 2-Pyridyl C₂H₅ 674 CH₃ 2-Pyridyl n-C₃H₇ 675 CH₃ 2-Pyridyl i-C₃H₇ 676 CH₃ 3-Pyridyl H 677 CH₃ 3-Pyridyl CH₃ 678 CH₃ 3-Pyridyl C₂H₅ 679 CH₃ 3-Pyridyl n-C₃H₇ 680 CH₃ 3-Pyridyl i-C₃H₇ 681 CH₃ 4-Pyridyl H 682 CH₃ 4-Pyridyl CH₃ 683 CH₃ 4-Pyridyl C₂H₅ 684 CH₃ 4-Pyridyl n-C₃H₇ 685 CH₃ 4-Pyridyl i-C₃H₇ 686 CH₃ 2-Pyridimidyl H 687 CH₃ 2-Pyridimidyl CH₃ 688 CH₃ 2-Pyridimidyl C₂H₅ 689 CH₃ 2-Pyridimidyl n-C₃H₇ 690 CH₃ 2-Pyridimidyl i-C₃H₇ 691 CH₃ 4-Pyridimidy H 692 CH₃ 4-Pyridimidyl CH₃ 693 CH₃ 4-Pyridimidyl C₂H₅ 694 CH₃ 4-Pyridimidyl n-C₃H₇ 695 CH₃ 4-Pyridimidyl i-C₃H₇ 696 CH₃ 5-Pyridimidyl H 697 CH₃ 5-Pyridimidyl CH₃ 698 CH₃ 5-Pyridimidyl C₂H₅ 699 CH₃ 5-Pyridimidyl n-C₃H₇ 700 CH₃ 5-Pyridimidyl i-C₃H₇ 701 CH₃ 1,3,5-Triazinyl H 702 CH₃ 1,3,5-Triazinyl CH₃ 703 CH₃ 1,3,5-Triazinyl C₂H₅ 704 CH₃ 1,3,5-Triazinyl n-C₃H₇ 705 CH₃ 1,3,5-Triazinyl i-C₃H₇ 706 CH₃ 2-Furyl H 707 CH₃ 2-Furyl CH₃ 708 CH₃ 2-Furyl C₂H₅ 709 CH₃ 2-Furyl n-C₃H₇ 710 CH₃ 2-Furyl i-C₃H₇ 711 CH₃ 3-Furyl H 712 CH₃ 3-Furyl CH₃ 713 CH₃ 3-Furyl C₂H₅ 714 CH₃ 3-Furyl n-C₃H₇ 715 CH₃ 3-Furyl i-C₃H₇ 716 CH₃ 2-Thienyl H 717 CH₃ 2-Thienyl CH₃ 718 CH₃ 2-Thienyl C₂H₅ 719 CH₃ 2-Thienyl n-C₃H₇ 720 CH₃ 2-Thienyl i-C₃H₇ 721 CH₃ 3-Thienyl H 722 CH₃ 3-Thienyl CH₃ 723 CH₃ 3-Thienyl C₂H₅ 724 CH₃ 3-Thienyl n-C₃H₇ 725 CH₃ 3-Thienyl i-C₃H₇ 726 CH₃ 2-Oxazolyl H 727 CH₃ 2-Oxazolyl CH₃ 728 CH₃ 2-Oxazolyl C₂H₅ 729 CH₃ 2-Oxazolyl n-C₃H₇ 730 CH₃ 2-Oxazolyl i-C₃H₇ 731 CH₃ 4-Oxazolyl H 732 CH₃ 4-Oxazolyl CH₃ 733 CH₃ 4-Oxazolyl C₂H₅ 734 CH₃ 4-Oxazolyl n-C₃H₇ 735 CH₃ 4-Oxazolyl i-C₃H₇ 736 CH₃ 2-Thiazolyl H 737 CH₃ 2-Thiazolyl CH₃ 738 CH₃ 2-Thiazolyl C₂H₅ 739 CH₃ 2-Thiazolyl n-C₃H₇ 740 CH₃ 2-Thiazolyl i-C₃H₇ 741 CH₃ 4-Thiazolyl H 742 CH₃ 4-Thiazolyl CH₃ 743 CH₃ 4-Thiazolyl C₂H₅ 744 CH₃ 4-Thiazolyl n-C₃H₇ 745 CH₃ 4-Thiazolyl i-C₃H₇ 746 CH₃ 3-Isoxazolyl H 747 CH₃ 3-Isoxazolyl CH₃ 748 CH₃ 3-Isoxazolyl C₂H₅ 749 CH₃ 3-Isoxazolyl n-C₃H₇ 750 CH₃ 3-Isoxazolyl i-C₃H₇ 751 CH₃ 5-Isoxazolyl H 752 CH₃ 5-Isoxazolyl CH₃ 753 CH₃ 5-Isoxazolyl C₂H₅ 754 CH₃ 5-Isoxazolyl n-C₃H₇ 755 CH₃ 5-Isoxazolyl i-C₃H₇ 756 CH₃ 2-Imidazolyl H 757 CH₃ 2-Imidazolyl CH₃ 758 CH₃ 2-Imidazolyl C₂H₅ 759 CH₃ 2-Imidazolyl n-C₃H₇ 760 CH₃ 2-Imidazolyl i-C₃H₇ 761 CH₃ 3-Pyrazolyl H 762 CH₃ 3-Pyrazolyl CH₃ 763 CH₃ 3-Pyrazolyl C₂H₅ 764 CH₃ 3-Pyrazolyl n-C₃H₇ 765 CH₃ 3-Pyrazolyl i-C₃H₇ 766 CH₃ 4-Pyrazolyl H 767 CH₃ 4-Pyrazolyl CH₃ 768 CH₃ 4-Pyrazolyl C₂H₅ 769 CH₃ 4-Pyrazolyl n-C₃H₇ 770 CH₃ 4-Pyrazolyl i-C₃H₇ 771 OCH₃ H H 772 OCH₃ H CH₃ 773 OCH₃ H C₂H₅ 774 OCH₃ H n-C₃H₇ 775 OCH₃ H i-C₃H₇ 776 OCH₃ OH H 777 OCH₃ OH CH₃ 776 OCH₃ OH C₂H₅ 779 OCH₃ OH n-C₃H₇ 780 OCH₃ OH i-C₃H₇ 781 OCH₃ Cl n-C₄H₉ 782 OCH₃ Cl CH₃ 783 OCH₃ Cl C₂H₅ 784 OCH₃ Cl n-C₃H₇ 785 OCH₃ Cl i-C₃H₇ 786 OCH₃ OCH₃ H 787 OCH₃ OCH₃ CH₃ 788 OCH₃ OCH₃ C₂H₅ 789 OCH₃ OCH₃ n-C₃H₇ 790 OCH₃ OCH₃ i-C₃H₇ 791 OCH₃ SCH₃ H 792 OCH₃ SCH₃ CH₃ 793 OCH₃ SCH₃ C₂H₅ 794 OCH₃ SCH₃ n-C₃H₇ 795 OCH₃ SCH₃ i-C₃H₇ 796 OCH₃ CH₃ H 797 OCH₃ CH₃ CH₃ 798 OCH₃ CH₃ C₂H₅ 799 OCH₃ CH₃ n-C₃H₇ 800 OCH₃ CH₃ i-C₃H₇ 801 OCH₃ Cyclopropyl H 802 OCH₃ Cyclopropyl CH₃ 803 OCH₃ Cyclopropyl C₂H₅ 804 OCH₃ Cyclopropyl n-C₃H₇ 805 OCH₃ Cyclopropyl i-C₃H₇ 806 OCH₃ 2-Pyridyl H 807 OCH₃ 2-Pyridyl CH₃ 808 OCH₃ 2-Pyridyl C₂H₅ 809 OCH₃ 2-Pyridyl n-C₃H₇ 810 OCH₃ 2-Pyridyl i-C₃H₇ 811 OCH₃ 3-Pyridyl H 812 OCH₃ 3-Pyridyl CH₃ 813 OCH₃ 3-Pyridyl C₂H₅ 814 OCH₃ 3-Pyridyl n-C₃H₇ 815 OCH₃ 3-Pyridyl i-C₃H₇ 816 OCH₃ 4-Pyridyl H 817 OCH₃ 4-Pyridyl CH₃ 818 OCH₃ 4-Pyridyl C₂H₅ 819 OCH₃ 4-Pyridyl n-C₃H₇ 820 OCH₃ 4-Pyrimidyl i-C₃H₇ 821 OCH₃ 2-Pyrimidyl H 822 OCH₃ 2-Pyrimidyl CH₃ 823 OCH₃ 2-Pyrimidyl C₂H₅ 824 OCH₃ 2-Pyrimidyl n-C₃H₇ 825 OCH₃ 2-Pyrimidyl i-C₃H₇ 826 OCH₃ 4-Pyrimidyl H 827 OCH₃ 4-Pyrimidyl CH₃ 828 OCH₃ 4-Pyrimidyl C₂H₅ 829 OCH₃ 4-Pyrimidyl n-C₃H₇ 830 OCH₃ 4-Pyrimidyl i-C₃H₇ 831 OCH₃ 5-Pyrimidyl H 832 OCH₃ 5-Pyrimidyl CH₃ 833 OCH₃ 5-Pyrimidyl C₂H₅ 834 OCH₃ 5-Pyrimidyl n-C₃H₇ 835 OCH₃ 5-Pyrimidyl i-C₃H₇ 836 OCH₃ 1,3,5-Triazinyl H 837 OCH₃ 1,3,5-Triazinyl CH₃ 838 OCH₃ 1,3,5-Triazinyl C₂H₅ 839 OCH₃ 1,3,5-Triazinyl n-C₃H₇ 840 OCH₃ 1,3,5-Triazinyl i-C₃H₇ 841 OCH₃ 2-Furyl H 842 OCH₃ 2-Furyl CH₃ 843 OCH₃ 2-Furyl C₂H₅ 844 OCH₃ 2-Furyl n-C₃H₇ 845 OCH₃ 2-Furyl i-C₃H₇ 846 OCH₃ 3-Furyl H 847 OCH₃ 3-Furyl CH₃ 848 OCH₃ 3-Furyl C₂H₅ 849 OCH₃ 3-Furyl n-C₃H₇ 850 OCH₃ 3-Furyl i-C₃H₇ 851 OCH₃ 2-Thienyl H 852 OCH₃ 2-Thienyl CH₃ 853 OCH₃ 2-Thienyl C₂H₅ 854 OCH₃ 2-Thienyl n-C₃H₇ 855 OCH₃ 2-Thienyl i-C₃H₇ 856 OCH₃ 3-Thienyl H 857 OCH₃ 3-Thienyl CH₃ 858 OCH₃ 3-Thienyl C₂H₅ 859 OCH₃ 3-Thienyl n-C₃H₇ 860 OCH₃ 3-Thienyl i-C₃H₇ 861 OCH₃ 2-Oxazolyl H 862 OCH₃ 2-Oxazolyl CH₃ 863 OCH₃ 2-Oxazolyl C₂H₅ 864 OCH₃ 2-Oxazolyl n-C₃H₇ 865 OCH₃ 2-Oxazolyl i-C₃H₇ 866 OCH₃ 4-Oxazolyl H 867 OCH₃ 4-Oxazolyl CH₃ 868 OCH₃ 4-Oxazolyl C₂H₅ 869 OCH₃ 4-Oxazolyl n-C₃H₇ 870 OCH₃ 4-Oxazolyl i-C₃H₇ 871 OCH₃ 2-Thiazolyl H 872 OCH₃ 2-Thiazolyl CH₃ 873 OCH₃ 2-Thiazolyl C₂H₅ 874 OCH₃ 2-Thiazolyl n-C₃H₇ 875 OCH₃ 2-Thiazolyl i-C₃H₇ 876 OCH₃ 4-Thiazolyl H 877 OCH₃ 4-Thiazolyl CH₃ 878 OCH₃ 4-Thiazolyl C₂H₅ 879 OCH₃ 4-Thiazolyl n-C₃H₇ 880 OCH₃ A-Thiazolyl i-C₃H₇ 881 OCH₃ 3-Isoxazolyl H 882 OCH₃ 3-Isoxazolyl CH₃ 883 OCH₃ 3-Isoxazolyl C₂H₅ 884 OCH₃ 3-Isoxazolyl n-C₃H₇ 885 OCH₃ 3-Isoxazolyl i-C₃H₇ 886 OCH₃ 5-Isoxazolyl H 887 OCH₃ 5-Isoxazolyl CH₃ 888 OCH₃ 5-Isoxazolyl C₂H₅ 889 OCH₃ 5-Isoxazolyl n-C₃H₇ 890 OCH₃ 5-Isoxazolyl i-C₃H₇ 891 OCH₃ 2-Imidazolyl H 892 OCH₃ 2-Imidazolyl CH₃ 893 OCH₃ 2-Imidazolyl C₂H₅ 894 OCH₃ 2-Imidazolyl n-C₃H₇ 895 OCH₃ 2-Imidazolyl i-C₃H₇ 896 OCH₃ 3-Pyrazolyl H 897 OCH₃ 3-Pyrazolyl CH₃ 898 OCH₃ 3-Pyrazolyl C₂H₅ 899 OCH₃ 3-Pyrazolyl n-C₃H₇ 900 OCH₃ 3-Pyrazolyl i-C₃H₇ 901 OCH₃ 4-Pyrazolyl H 902 OCH₃ 4-Pyrazolyl CH₃ 903 OCH₃ 4-Pyrazolyl C₂H₅ 904 OCH₃ 4-Pyrazolyl n-C₃H₇ 905 OCH₃ 4-Pyrazolyl i-C₃H₇ 906 OH H H 907 OH H CH₃ 908 OH H C₂H₅ 909 OH H n-C₃H₇ 910 OH H i-C₃H₇ 911 OH OH H 912 OH OH CH₃ 913 OH OH C₂H₅ 914 OH OH n-C₃H₇ 915 OH OH i-C₃H₇ 916 OH Cl n-C₄H₉ 917 OH Cl CH₃ 918 OH Cl C₂H₅ 919 OH Cl n-C₃H₇ 920 OH Cl i-C₃H₇ 921 OH OCH₃ H 922 OH OCH₃ CH₃ 923 OH OCH₃ C₂H₅ 924 OH OCH₃ n-C₃H₇ 925 OH OCH₃ i-C₃H₇ 926 OH SCH₃ H 927 OH SCH₃ CH₃ 928 OH SCH₃ C₂H₅ 929 OH SCH₃ n-C₃H₇ 930 OH SCH₃ i-C₃H₇ 931 OH CH₃ H 932 OH CH₃ CH₃ 933 OH CH₃ C₂H₅ 934 OH CH₃ n-C₃H₇ 935 OH CH₃ i-C₃H₇ 936 OH Cyclopropyl H 937 OH Cyclopropyl CH₃ 938 OH Cyclopropyl C₂H₅ 939 OH Cyclopropyl n-C₃H₇ 940 OH Cyclopropyl i-C₃H₇ 941 OH 2-Pyridyl H 942 OH 2-Pyridyl CH₃ 943 OH 2-Pyridyl C₂H₅ 944 OH 2-Pyridyl n-C₃H₇ 945 OH 2-Pyridyl i-C₃H₇ 946 OH 3-Pyridyl H 947 OH 3-Pyridyl CH₃ 948 OH 3-Pyridyl C₂H₅ 949 OH 3-Pyridyl n-C₃H₇ 950 OH 3-Pyridyl i-C₃H₇ 951 OH 4-Pyridyl H 952 OH 4-Pyridyl CH₃ 953 OH 4-Pyridyl C₂H₅ 954 OH 4-Pyridyl n-C₃H₇ 955 OH 4-Pyridyl i-C₃H₇ 956 OH 2-Pyrimidyl H 957 OH 2-Pyrimidyl CH₃ 958 OH 2-Pyrimidyl C₂H₅ 959 OH 2-Pyrimidyl n-C₃H₇ 960 OH 2-Pyrimidyl i-C₃H₇ 961 OH 4-Pyrimidyl H 962 OH 4-Pyrimidyl CH₃ 963 OH 4-Pyrimidyl C₂H₅ 964 OH 4-Pyrimidyl n-C₃H₇ 965 OH 4-Pyrimidyl i-C₃H₇ 966 OH 5-Pyrimidyl H 967 OH 5-Pyrimidyl CH₃ 968 OH 5-Pyrimidyl C₂H₅ 969 OH 5-Pyrimidyl n-C₃H₇ 970 OH 5-Pyrimidyl i-C₃H₇ 971 OH 1,3,5-Triazinyl H 972 OH 1,3,5-Triazinyl CH₃ 973 OH 1,3,5-Triazinyl C₂H₅ 974 OH 1,3,5-Triazinyl n-C₃H₇ 975 OH 1,3,5-Triazinyl i-C₃H₇ 976 OH 2-Furyl H 977 OH 2-Furyl CH₃ 978 OH 2-Furyl C₂H₅ 979 OH 2-Furyl n-C₃H₇ 980 OH 2-Furyl i-C₃H₇ 981 OH 3-Furyl H 982 OH 3-Furyl CH₃ 983 OH 3-Furyl C₂H₅ 984 OH 3-Furyl n-C₃H₇ 985 OH 3-Furyl i-C₃H₇ 986 OH 2-Thienyl H 987 OH 2-Thienyl CH₃ 988 OH 2-Thienyl C₂H₅ 989 OH 2-Thienyl n-C₃H₇ 990 OH 2-Thienyl i-C₃H₇ 991 OH 3-Thienyl H 992 OH 3-Thienyl CH₃ 993 OH 3-Thienyl C₂H₅ 994 OH 3-Thienyl n-C₃H₇ 995 OH 3-Thienyl i-C₃H₇ 996 OH 2-Oxazolyl H 997 OH 2-Oxazolyl CH₃ 998 OH 2-Oxazolyl C₂H₅ 999 OH 2-Oxazolyl n-C₃H₇ 1000 OH 2-Oxazolyl i-C₃H₇ 1001 OH 4-Oxazolyl H 1002 OH 4-Oxazolyl CH₃ 1003 OH 4-Oxazolyl C₂H₅ 1004 QH 4-Oxazolyl n-C₃H₇ 1005 OH 2-Thiazolyl i-C₃H₇ 1006 OH 2-Thiazolyl H 1007 OH 2-Thiazolyl CH₃ 1008 OH 2-Thiazolyl C₂H₅ 1009 OH 2-Thiazolyl n-C₃H₇ 1010 OH 2-Thiazolyl i-C₃H₇ 1011 OH 4-Thiazolyl H 1012 OH 4-Thiazolyl CH₃ 1013 OH 4-Thiazolyl C₂H₅ 1014 OH 4-Isoxazolyl n-C₃H₇ 1015 OH 4-Isoxazolyl i-C₃H₇ 1016 OH 3-Isoxazolyl H 1017 OH 3-Isoxazolyl CH₃ 1018 OH 3-Isoxazolyl C₂H₅ 1019 OH 3-Isoxazolyl n-C₃H₇ 1020 OH 3-Isoxazolyl i-C₃H₇ 1021 OH 5-Isoxazolyl H 1022 OH 5-Isoxazolyl CH₃ 1023 OH 5-Isoxazolyl C₂H₅ 1024 OH 5-Isoxazolyl n-C₃H₇ 1025 OH 5-Isoxazolyl i-C₃H₇ 1026 OH 2-Imidazolyl H 1027 OH 2-Imidazolyl CH₃ 1028 OH 2-Imidazolyl C₂H₅ 1029 OH 2-Imidazolyl n-C₃H₇ 1030 OH 2-Imidazolyl i-C₃H₇ 1031 OH 3-Pyrazolyl H 1032 OH 3-Pyrazolyl CH₃ 1033 OH 3-Pyrazolyl C₂H₅ 1034 OH 3-Pyrazolyl n-C₃H₇ 1035 OH 3-Pyrazolyl i-C₃H₇ 1036 OH 4-Pyrazolyl H 1037 OH 4-Pyrazolyl CH₃ 1038 OH 4-Pyrazolyl C₂H₅ 1039 OH 4-Pyrazolyl n-C₃H₇ 1040 OH 4-Pyrazolyl i-C₃H₇ 1041 H H H 1042 H H CH₃ 1043 H H C₂H₅ 1044 H H n-C₃H₇ 1045 H H i-C₃H₇ 1046 H OH H 1047 H OH CH₃ 1048 H OH C₂H₅ 1049 H OH n-C₃H₇ 1050 H OH i-C₃H₇ 1051 H Cl n-C₄H₉ 1052 H Cl CH₃ 1053 H Cl C₂H₅ 1054 H Cl n-C₃H₇ 1055 H Cl i-C₃H₇ 1056 H OCH₃ H 1057 H OCH₃ CH₃ 1058 H OCH₃ C₂H₅ 1059 H OCH₃ n-C₃H₇ 1060 H OCH₃ i-C₃H₇ 1061 H CH₃ H 1062 H CH₃ CH₃ 1063 H CH₃ C₂H₅ 1064 H CH₃ n-C₃H₇ 1065 H CH₃ i-C₃H₇ 1066 H Cyclopropyl H 1067 H Cyclopropyl CH₃ 1068 H Cyclopropyl C₂H₅ 1069 H Cyclopropyl n-C₃H₇ 1070 H Cyclopropyl i-C₃H₇ 1071 Cl H H 1072 Cl H CH₃ 1073 Cl H C₂H₅ 1074 Cl H n-C₃H₇ 1075 Cl H i-C₃H₇ 1076 Cl OH H 1077 Cl OH CH₃ 1078 Cl OH C₂H₅ 1079 Cl OH n-C₃H₇ 1080 Cl OH i-C₃H₇ 1081 Cl Cl n-C₄H₉ 1082 Cl Cl CH₃ 1083 Cl Cl C₂H₅ 1084 Cl Cl n-C₃H₇ 1085 Cl Cl i-C₃H₇ 1086 Cl OCH₃ H 1087 Cl OCH₃ CH₃ 1088 Cl OCH₃ C₂H₅ 1089 Cl OCH₃ n-C₃H₇ 1090 Cl OCH₃ i-C₃H₇ 1091 Cl CH₃ H 1092 Cl CH₃ CH₃ 1093 Cl CH₃ C₂H₅ 1094 Cl CH₃ n-C₃H₇ 1095 Cl CH₃ i-C₃H₇ 1096 Cl Cyclopropyl H 1097 Cl Cyclopropyl CH₃ 1098 Cl Cyclopropyl C₂H₅ 1099 Cl Cyclopropyl n-C₃H₇ 1100 Cl Cyclopropyl i-C₃H₇ 1101 SCH₃ H H 1102 SCH₃ H CH₃ 1103 SCH₃ H C₂H₅ 1104 SCH₃ H n-C₃H₇ 1105 SCH₃ H i-C₃H₇ 1106 SCH₃ OH H 1107 SCH₃ OH CH₃ 1108 SCH₃ OH C₂H₅ 1109 SCH₃ OH n-C₃H₇ 1110 SCH₃ OH i-C₃H₇ 1111 SCH₃ CH₃ H 1112 SCH₃ CH₃ CH₃ 1113 SCH₃ CH₃ C₂H₅ 1114 SCH₃ CH₃ n-C₃H₇ 1115 SCH₃ CH₃ i-C₃H₇ 1116 SCH₃ SCH₃ H 1117 SCH₃ SCH₃ CH₃ 1118 SCH₃ SCH₃ C₂H₅ 1119 SCH₃ SCH₃ n-C₃H₇ 1120 SCH₃ SCH₃ i-C₃H₇ 1121 SCH₃ Cyclopropyl H 1122 SCH₃ Cyclopropyl CH₃ 1123 SCH₃ Cyclopropyl C₂H₅ 1124 SCH₃ Cyclopropyl n-C₃H₇ 1125 SCH₃ Cyclopropyl i-C₃H₇ 1126 Cyclo- H H propyl 1127 Cyclo- H CH₃ propyl 1128 Cyclo- H C₂H₅ propyl 1129 Cyclo- H n-C₃H₇ propyl 1130 Cyclo- H i-C₃H₇ propyl 1131 Cyclo- OH H propyl 1132 Cyclo- OH CH₃ propyl 1133 Cyclo- OH C₂H₅ propyl 1134 Cyclo- OH n-C₃H₇ propyl 1135 Cyclo- OH i-C₃H₇ propyl 1136 Cyclo- Cl n-C₄H₉ propyl 1137 Cyclo- Cl CH₃ propyl 1138 Cyclo- Cl C₂H₅ propyl 1139 Cyclo- Cl n-C₃H₇ propyl 1140 Cyclo- Cl i-C₃H₇ propyl 1141 Cyclo- OCH₃ H propyl 1142 Cyclo- OCH₃ CH₃ propyl 1143 Cyclo- OCH₃ C₂H₅ propyl 1144 Cyclo- OCH₃ n-C₃H₇ propyl 1145 Cyclo- OCH₃ i-C₃H₇ propyl 1146 Cyclo- SCH₃ H propyl 1147 Cyclo- SCH₃ CH₃ propyl 1148 Cyclo- SCH₃ C₂H₅ propyl 1149 Cyclo- SCH₃ n-C₃H₇ propyl 1150 Cyclo- SCH₃ i-C₃H₇ propyl 1151 Cyclo- CH₃ H propyl 1152 Cyclo- CH₃ CH₃ propyl 1153 Cyclo- CH₃ C₂H₅ propyl 1154 Cyclo- CH₃ n-C₃H₇ propyl 1155 Cyclo- CH₃ i-C₃H₇ propyl 1156 CH₃ 2-F—C₆H₄ CH₃ 1157 CH₃ 2-F—C₆H₄ C₂H₅ 1158 CH₃ 2-F—C₆H₄ n-C₃H₇ 1159 CH₃ 2-F—C₆H₄ i-C₃H₇ 1160 CH₃ 2-F—C₆H₄ n-C₄H₉ 1161 CH₃ 2-F—C₆H₄ t-C₄H₉ 1162 CH₃ 2-F—C₆H₄ n-C₆H₁₃ 1163 CH₃ 2-F—C₆H₄ Prop-1-en-3-yl 1164 CH₃ 2-F—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1165 CH₃ 2-F—C₆H₄ Propyn-3-yl 1166 CH₃ 2-F—C₆H₄ 3-Methyl-but-2-en-1-yl 1167 CH₃ 3-F—C₆H₄ H 1168 CH₃ 3-F—C₆H₄ CH₃ 1169 CH₃ 3-F—C₆H₄ C₂H₅ 1170 CH₃ 3-F—C₆H₄ n-C₃H₇ 1171 CH₃ 3-F—C₆H₄ i-C₃H₇ 1172 CH₃ 3-F—C₆H₄ n-C₄H₉ 1173 CH₃ 3-F—C₆H₄ t-C₄H₉ 1174 CH₃ 3-F—C₆H₄ n-C₆H₁₃ 1175 CH₃ 3-F—C₆H₄ Prop-1-en-3-yl 1176 CH₃ 3-F—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1177 CH₃ 3-F—C₆H₄ Propyn-3-yl 1178 CH₃ 3-F—C₆H₄ 3-Methyl-but-2-en-1-yl 1179 CH₃ 4-F—C₆H₄ H 1180 CH₃ 4-F—C₆H₄ CH₃ 1181 CH₃ 4-F—C₆H₄ C₂H₅ 1182 CH₃ 4-F—C₆H₄ n-C₃H₇ 1183 CH₃ 4-F—C₆H₄ i-C₃H₇ 1184 CH₃ 4-F—C₆H₄ n-C₄H₉ 1185 CH₃ 4-F—C₆H₄ t-C₄H₉ 1186 CH₃ 4-F—C₆H₄ n-C₆H₁₃ 1187 CH₃ 4-F—C₆H₄ Prop-1-en-3-yl 1188 CH₃ 4-F—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1189 CH₃ 4-F—C₆H₄ Propyn-3-yl 1190 CH₃ 4-F—C₆H₄ 3-Methyl-but-2-en-1-yl 1191 CH₃ 2-Cl—C₆H₄ H 1192 CH₃ 2-Cl—C₆H₄ CH₃ 1193 CH₃ 2-Cl—C₆H₄ C₂H₅ 1194 CH₃ 2-Cl—C₆H₄ n-C₃H₇ 1195 CH₃ 2-Cl—C₆H₄ i-C₃H₇ 1196 CH₃ 2-Cl—C₆H₄ n-C₄H₉ 1197 CH₃ 2-Cl—C₆H₄ t-C₄H₉ 1198 CH₃ 2-Cl—C₆H₄ n-C₆H₁₃ 1199 CH₃ 2-Cl—C₆H₄ Prop-1-en-3-yl 1200 CH₃ 2-Cl—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1201 CH₃ 2-Cl—C₆H₄ Propyn-3-yl 1202 CH₃ 2-Cl—C₆H₄ 3-Methyl-but-2-en-1-yl 1203 CH₃ 3-Cl—C₆H₄ H 1204 CH₃ 3-Cl—C₆H₄ CH₃ 1205 CH₃ 3-Cl—C₆H₄ C₂H₅ 1206 CH₃ 3-Cl—C₆H₄ n-C₃H₇ 1207 CH₃ 3-Cl—C₆H₄ i-C₃H₇ 1208 CH₃ 3-Cl—C₆H₄ n-C₄H₉ 1209 CH₃ 3-Cl—C₆H₄ t-C₄H₉ 1210 CH₃ 3-Cl—C₆H₄ n-C₆H₁₃ 1211 CH₃ 3-Cl—C₆H₄ Prop-1-en-3-yl 1212 CH₃ 3-Cl—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1213 CH₃ 3-Cl—C₆H₄ Propyn-3-yl 1214 CH₃ 3-Cl—C₆H₄ 3-Methyl-but-2-en-1-yl 1215 CH₃ 4-Cl—C₆H₄ H 1216 CH₃ 4-Cl—C₆H₄ CH₃ 1217 CH₃ 4-Cl—C₆H₄ C₂H₅ 1218 CH₃ 4-Cl—C₆H₄ n-C₃H₇ 1219 CH₃ 4-Cl—C₆H₄ i-C₃H₇ 1220 CH₃ 4-Cl—C₆H₄ n-C₄H₉ 1221 CH₃ 4-Cl—C₆H₄ t-C₄H₉ 1222 CH₃ 4-Cl—C₆H₄ n-C₆H₁₃ 1223 CH₃ 4-Cl—C₆H₄ Prop-1-en-3-yl 1224 CH₃ 4-Cl—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1225 CH₃ 4-Cl—C₆H₄ Propyn-3-yl 1226 CH₃ 4-Cl—C₆H₄ 3-Methyl-but-2-en-1-yl 1227 CH₃ 2,3-Cl₂—C₆H₃ H 1228 CH₃ 2,3-Cl₂—C₆H₃ CH₃ 1229 CH₃ 2,3-Cl₂—C₆H₃ C₂H₅ 1230 CH₃ 2,3-Cl₂—C₆H₃ n-C₃H₇ 1231 CH₃ 2,3-Cl₂—C₆H₃ i-C₃H₇ 1232 CH₃ 2,3-Cl₂—C₆H₃ n-C₄H₉ 1233 CH₃ 2,3-Cl₂—C₆H₃ t-C₄H₉ 1234 CH₃ 2,3-Cl₂—C₆H₃ n-C₆H₁₃ 1235 CH₃ 2,3-Cl₂—C₆H₃ Prop-1-en-3-yl 1236 CH₃ 2,3-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1237 CH₃ 2,3-Cl₂—C₆H₃ Propyn-3-yl 1238 CH₃ 2,3-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1239 CH₃ 2,4-Cl₂—C₆H₃ H 1240 CH₃ 2,4-Cl₂—C₆H₃ CH₃ 1241 CH₃ 2,4-Cl₂—C₆H₃ C₂H₅ 1242 CH₃ 2,4-Cl₂—C₆H₃ n-C₃H₇ 1243 CH₃ 2,4-Cl₂—C₆H₃ i-C₃H₇ 1244 CH₃ 2,4-Cl₂—C₆H₃ n-C₄H₉ 1245 CH₃ 2,4-Cl₂—C₆H₃ t-C₄H₉ 1246 CH₃ 2,4-Cl₂—C₆H₃ n-C₆H₁₃ 1247 CH₃ 2,4-Cl₂—C₆H₃ Prop-1-en-3-yl 1248 CH₃ 2,4-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1249 CH₃ 2,4-Cl₂—C₆H₃ Propyn-3-yl 1250 CH₃ 2,4-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1251 CH₃ 2,5-Cl₂—C₆H₃ H 1252 CH₃ 2,5-Cl₂—C₆H₃ CH₃ 1253 CH₃ 2,5-Cl₂—C₆H₃ C₂H₅ 1254 CH₃ 2,5-Cl₂—C₆H₃ n-C₃H₇ 1255 CH₃ 2,5-Cl₂—C₆H₃ i-C₃H₇ 1256 CH₃ 2,5-Cl₂—C₆H₃ n-C₄H₉ 1257 CH₃ 2,5-Cl₂—C₆H₃ t-C₄H₉ 1258 CH₃ 2,5-Cl₂—C₆H₃ n-C₆H₁₃ 1259 CH₃ 2,5-Cl₂—C₆H₃ Prop-1-en-3-yl 1260 CH₃ 2,5-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1261 CH₃ 2,5-Cl₂—C₆H₃ Propyn-3-yl 1262 CH₃ 2,5-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1263 CH₃ 2,6-Cl₂—C₆H₃ H 1264 CH₃ 2,6-Cl₂—C₆H₃ CH₃ 1265 CH₃ 2,6-Cl₂—C₆H₃ C₂H₅ 1266 CH₃ 2,6-Cl₂—C₆H₃ n-C₃H₇ 1267 CH₃ 2,6-Cl₂—C₆H₃ i-C₃H₇ 1268 CH₃ 2,6-Cl₂—C₆H₃ n-C₄H₉ 1269 CH₃ 2,6-Cl₂—C₆H₃ t-C₄H₉ 1270 CH₃ 2,6-Cl₂—C₆H₃ n-C₆H₁₃ 1271 CH₃ 2,6-Cl₂—C₆H₃ Prop-1-en-3-yl 1272 CH₃ 2,6-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1273 CH₃ 2,6-Cl₂—C₆H₃ Propyn-3-yl 1274 CH₃ 2,6-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1275 CH₃ 3,4-Cl₂—C₆H₃ H 1276 CH₃ 3,4-Cl₂—C₆H₃ CH₃ 1277 CH₃ 3,4-Cl₂—C₆H₃ C₂H₅ 1278 CH₃ 3,4-Cl₂—C₆H₃ n-C₃H₇ 1279 CH₃ 3,4-Cl₂—C₆H₃ i-C₃H₇ 1280 CH₃ 3,4-Cl₂—C₆H₃ n-C₄H₉ 1281 CH₃ 3,4-Cl₂—C₆H₃ t-C₄H₉ 1282 CH₃ 3,4-Cl₂—C₆H₃ n-C₆H₁₃ 1283 CH₃ 3,4-Cl₂—C₆H₃ Prop-1-en-3-yl 1284 CH₃ 3,4-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1285 CH₃ 3,4-Cl₂—C₆H₃ Propyn-3-yl 1286 CH₃ 3,4-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1287 CH₃ 3,5-Cl₂—C₆H₃ H 1288 CH₃ 3,5-Cl₂—C₆H₃ CH₃ 1289 CH₃ 3,5-Cl₂—C₆H₃ C₂H₅ 1290 CH₃ 3,5-Cl₂—C₆H₃ n-C₃H₇ 1291 CH₃ 3,5-Cl₂—C₆H₃ i-C₃H₇ 1292 CH₃ 3,5-Cl₂—C₆H₃ n-C₄H₉ 1293 CH₃ 3,5-Cl₂—C₆H₃ t-C₄H₉ 1294 CH₃ 3,5-Cl₂—C₆H₃ n-C₆H₁₃ 1295 CH₃ 3,5-Cl₂—C₆H₃ Prop-1-en-3-yl 1296 CH₃ 3,5-Cl₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1297 CH₃ 3,5-Cl₂—C₆H₃ Propyn-3-yl 1298 CH₃ 3,5-Cl₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1299 CH₃ 2-Br—C₆H₄ H 1300 CH₃ 2-Br—C₆H₄ CH₃ 1301 CH₃ 2-Br—C₆H₄ C₂H₅ 1302 CH₃ 2-Br—C₆H₄ n-C₃H₇ 1303 CH₃ 2-Br—C₆H₄ i-C₃H₇ 1304 CH₃ 2-Br—C₆H₄ n-C₄H₉ 1305 CH₃ 2-Br—C₆H₄ t-C₄H₉ 1306 CH₃ 2-Br—C₆H₄ n-C₆H₁₃ 1307 CH₃ 2-Br—C₆H₄ Prop-1-en-3-yl 1308 CH₃ 2-Br—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1309 CH₃ 2-Br—C₆H₄ Propyn-3-yl 1310 CH₃ 2-Br—C₆H₄ 3-Methyl-but-2-en-1-yl 1311 CH₃ 3-Br—C₆H₄ H 1312 CH₃ 3-Br—C₆H₄ CH₃ 1313 CH₃ 3-Br—C₆H₄ C₂H₅ 1314 CH₃ 3-Br—C₆H₄ n-C₃H₇ 1315 CH₃ 3-Br—C₆H₄ i-C₃H₇ 1316 CH₃ 3-Br—C₆H₄ n-C₄H₉ 1317 CH₃ 3-Br—C₆H₄ t-C₄H₉ 1318 CH₃ 3-Br—C₆H₄ n-C₆H₁₃ 1319 CH₃ 3-Br—C₆H₄ Prop-1-en-3-yl 1320 CH₃ 3-Br—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1321 CH₃ 3-Br—C₆H₄ Propyn-3-yl 1322 CH₃ 3-Br—C₆H₄ 3-Methyl-but-2-en-1-yl 1323 CH₃ 4-Br—C₆H₄ H 1324 CH₃ 4-Br—C₆H₄ CH₃ 1325 CH₃ 4-Br—C₆H₄ C₂H₅ 1326 CH₃ 4-Br—C₆H₄ n-C₃H₇ 1327 CH₃ 4-Br—C₆H₄ i-C₃H₇ 1326 CH₃ 4-Br—C₆H₄ n-C₄H₉ 1329 CH₃ 4-Br—C₆H₄ t-C₄H₉ 1330 CH₃ 4-Br—C₆H₄ n-C₆H₁₃ 1331 CH₃ 4-Br—C₆H₄ Prop-1-en-3-yl 1332 CH₃ 4-Br—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1333 CH₃ 4-Br—C₆H₄ Propyn-3-yl 1334 CH₃ 4-Br—C₆H₄ 3-Methyl-but-2-en-1-yl 1335 CH₃ 2-I—C₄H₄ H 1336 CH₃ 2-I—C₄H₄ CH₃ 1337 CH₃ 2-I—C₄H₄ C₂H₅ 1338 CH₃ 2-I—C₄H₄ n-C₃H₇ 1339 CH₃ 2-I—C₄H₄ i-C₃H₇ 1340 CH₃ 2-I—C₄H₄ n-C₄H₉ 1341 CH₃ 2-I—C₄H₄ t-C₄H₉ 1342 CH₃ 2-I—C₄H₄ n-C₆H₁₃ 1343 CH₃ 2-I—C₄H₄ Prop-1-en-3-yl 1344 CH₃ 2-I—C₄H₄ (E)-1-Chloroprop-1-en-3-yl 1345 CH₃ 2-I—C₄H₄ Propyn-3-yl 1346 CH₃ 2-I—C₄H₄ 3-Methyl-but-2-en-1-yl 1347 CH₃ 3-I—C₄H₄ H 1348 CH₃ 3-I—C₄H₄ CH₃ 1349 CH₃ 3-I—C₄H₄ C₂H₅ 1350 CH₃ 3-I—C₄H₄ n-C₃H₇ 1351 CH₃ 3-I—C₄H₄ i-C₃H₇ 1352 CH₃ 3-I—C₄H₄ n-C₄H₉ 1353 CH₃ 3-I—C₄H₄ t-C₄H₉ 1354 CH₃ 3-I—C₄H₄ n-C₆H₁₃ 1355 CH₃ 3-I—C₄H₄ Prop-1-en-3-yl 1356 CH₃ 3-I—C₄H₄ (E)-1-Chloroprop-1-en-3-yl 1357 CH₃ 3-I—C₄H₄ Propyn-3-yl 1358 CH₃ 3-I—C₄H₄ 3-Methyl-but-2-en-1-yl 1359 CH₃ 4-I—C₄H₄ H 1360 CH₃ 4-I—C₄H₄ CH₃ 1361 CH₃ 4-I—C₄H₄ C₂H₅ 1362 CH₃ 4-I—C₄H₄ n-C₃H₇ 1363 CH₃ 4-I—C₄H₄ i-C₃H₇ 1364 CH₃ 4-I—C₄H₄ n-C₄H₉ 1365 CH₃ 4-I—C₄H₄ t-C₄H₉ 1366 CH₃ 4-I—C₄H₄ n-C₆H₁₃ 1367 CH₃ 4-I—C₄H₄ Prop-1-en-3-yl 1368 CH₃ 4-I—C₄H₄ (E)-1-Chloroprop-1-en-3-yl 1369 CH₃ 4-I—C₄H₄ Propyn-3-yl 1370 CH₃ 4-I—C₄H₄ 3-Methyl-but-2-en-1-yl 1371 CH₃ 2-CN—C₆H₄ H 1372 CH₃ 2-CN—C₆H₄ CH₃ 1373 CH₃ 2-CN—C₆H₄ C₂H₅ 1374 CH₃ 2-CN—C₆H₄ n-C₃H₇ 1375 CH₃ 2-CN—C₆H₄ i-C₃H₇ 1376 CH₃ 2-CN—C₆H₄ n-C₄H₉ 1377 CH₃ 2-CN—C₆H₄ t-C₄H₉ 1378 CH₃ 2-CN—C₆H₄ n-C₆H₁₃ 1379 CH₃ 2-CN—C₆H₄ Prop-1-en-3-yl 1380 CH₃ 2-CN—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1381 CH₃ 2-CN—C₆H₄ Propyn-3-yl 1382 CH₃ 2-CN—C₆H₄ 3-Methyl-but-2-en-1-yl 1383 CH₃ 3-CN—C₆H₄ H 1364 CH₃ 3-CN—C₆H₄ CH₃ 1385 CH₃ 3-CN—C₆H₄ C₂H₅ 1386 CH₃ 3-CN—C₆H₄ n-C₃H₇ 1387 CH₃ 3-CN—C₆H₄ i-C₃H₇ 1388 CH₃ 3-CN—C₆H₄ n-C₄H₉ 1389 CH₃ 3-CN—C₆H₄ t-C₄H₉ 1390 CH₃ 3-CN—C₆H₄ n-C₆H₁₃ 1391 CH₃ 3-CN—C₆H₄ Prop-1-en-3-yl 1392 CH₃ 3-CN—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1393 CH₃ 3-CN—C₆H₄ Propyn-3-yl 1394 CH₃ 3-CN—C₆H₄ 3-Methyl-but-2-en-1-yl 1395 CH₃ 4-CN—C₆H₄ H 1396 CH₃ 4-CN—C₆H₄ CH₃ 1397 CH₃ 4-CN—C₆H₄ C₂H₅ 1398 CH₃ 4-CN—C₆H₄ n-C₃H₇ 1399 CH₃ 4-CN—C₆H₄ i-C₃H₇ 1400 CH₃ 4-CN—C₆H₄ n-C₄H₉ 1401 CH₃ 4-CN—C₆H₄ t-C₄H₉ 1402 CH₃ 4-CN—C₆H₄ n-C₆H₁₃ 1403 CH₃ 4-CN—C₆H₄ Prop-1-en-3-yl 1404 CH₃ 4-CN—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1405 CH₃ 4-CN—C₆H₄ Propyn-3-yl 1406 CH₃ 4-CN—C₆H₄ 3-Methyl-but-2-en-1-yl 1407 CH₃ 2-NO₂—C₆H₄ H 1408 CH₃ 2-NO₂—C₆H₄ CH₃ 1409 CH₃ 2-NO₂—C₆H₄ C₂H₅ 1410 CH₃ 2-NO₂—C₆H₄ n-C₃H₇ 1411 CH₃ 2-NO₂—C₆H₄ i-C₃H₇ 1412 CH₃ 2-NO₂—C₆H₄ n-C₄H₉ 1413 CH₃ 2-NO₂—C₆H₄ t-C₄H₉ 1414 CH₃ 2-NO₂—C₆H₄ n-C₆H₁₃ 1415 CH₃ 2-NO₂—C₆H₄ Prop-1-en-3-yl 1416 CH₃ 2-NO₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1417 CH₃ 2-NO₂—C₆H₄ Propyn-3-yl 1418 CH₃ 2-NO₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1419 CH₃ 3-NO₂—C₆H₄ H 1420 CH₃ 3-NO₂—C₆H₄ CH₃ 1421 CH₃ 3-NO₂—C₆H₄ C₂H₅ 1422 CH₃ 3-NO₂—C₆H₄ n-C₃H₇ 1423 CH₃ 3-NO₂—C₆H₄ i-C₃H₇ 1424 CH₃ 3-NO₂—C₆H₄ n-C₄H₉ 1425 CH₃ 3-NO₂—C₆H₄ t-C₄H₉ 1426 CH₃ 3-NO₂—C₆H₄ n-C₆H₁₃ 1427 CH₃ 3-NO₂—C₆H₄ Prop-1-en-3-yl 1428 CH₃ 3-NO₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1429 CH₃ 3-NO₂—C₆H₄ Propyn-3-yl 1430 CH₃ 3-NO₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1431 CH₃ 4-NO₂—C₆H₄ H 1432 CH₃ 4-NO₂—C₆H₄ CH₃ 1433 CH₃ 4-NO₂—C₆H₄ C₂H₅ 1434 CH₃ 4-NO₂—C₆H₄ n-C₃H₇ 1435 CH₃ 4-NO₂—C₆H₄ i-C₃H₇ 1436 CH₃ 4-NO₂—C₆H₄ n-C₄H₉ 1437 CH₃ 4-NO₂—C₆H₄ t-C₄H₉ 1438 CH₃ 4-NO₂—C₆H₄ n-C₆H₁₃ 1439 CH₃ 4-NO₂—C₆H₄ Prop-1-en-3-yl 1440 CH₃ 4-NO₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1441 CH₃ 4-NO₂—C₆H₄ Propyn-3-yl 1442 CH₃ 4-NO₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1443 CH₃ 2-CH₃—C₆H₄ H 1444 CH₃ 2-CH₃—C₆H₄ CH₃ 1445 CH₃ 2-CH₃—C₆H₄ C₂H₅ 1446 CH₃ 2-CH₃—C₆H₄ n-C₃H₇ 1447 CH₃ 2-CH₃—C₆H₄ i-C₃H₇ 1448 CH₃ 2-CH₃—C₆H₄ n-C₄H₉ 1449 CH₃ 2-CH₃—C₆H₄ t-C₄H₉ 1450 CH₃ 2-CH₃—C₆H₄ n-C₆H₁₃ 1451 CH₃ 2-CH₃—C₆H₄ Prop-1-en-3-yl 1452 CH₃ 2-CH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1453 CH₃ 2-CH₃—C₆H₄ Propyn-3-yl 1454 CH₃ 2-CH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1455 CH₃ 3-CH₃—C₆H₄ H 1456 CH₃ 3-CH₃—C₆H₄ CH₃ 1457 CH₃ 3-CH₃—C₆H₄ C₂H₅ 1458 CH₃ 3-CH₃—C₆H₄ n-C₃H₇ 1459 CH₃ 3-CH₃—C₆H₄ i-C₃H₇ 1460 CH₃ 3-CH₃—C₆H₄ n-C₄H₉ 1461 CH₃ 3-CH₃—C₆H₄ t-C₄H₉ 1462 CH₃ 3-CH₃—C₆H₄ n-C₆H₁₃ 1463 CH₃ 3-CH₃—C₆H₄ Prop-1-en-3-yl 1464 CH₃ 3-CH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1465 CH₃ 3-CH₃—C₆H₄ Propyn-3-yl 1466 CH₃ 3-CH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1467 CH₃ 4-CH₃—C₆H₄ H 1468 CH₃ 4-CH₃—C₆H₄ CH₃ 1469 CH₃ 4-CH₃—C₆H₄ C₂H₅ 1470 CH₃ 4-CH₃—C₆H₄ n-C₃H₇ 1471 CH₃ 4-CH₃—C₆H₄ i-C₃H₇ 1472 CH₃ 4-CH₃—C₆H₄ n-C₄H₉ 1473 CH₃ 4-CH₃—C₆H₄ t-C₄H₉ 1474 CH₃ 4-CH₃—C₆H₄ n-C₆H₁₃ 1475 CH₃ 4-CH₃—C₆H₄ Prop-1-en-3-yl 1476 CH₃ 4-CH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1477 CH₃ 4-CH₃—C₆H₄ Propyn-3-yl 1478 CH₃ 4-CH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1479 CH₃ 2,3-(CH₃)₂—C₆H₃ H 1480 CH₃ 2,3-(CH₃)₂—C₆H₃ CH₃ 1481 CH₃ 2,3-(CH₃)₂—C₆H₃ C₂H₅ 1482 CH₃ 2,3-(CH₃)₂—C₆H₃ n-C₃H₇ 1483 CH₃ 2,3-(CH₃)₂—C₆H₃ i-C₃H₇ 1484 CH₃ 2,3-(CH₃)₂—C₆H₃ n-C₄H₉ 1485 CH₃ 2,3-(CH₃)₂—C₆H₃ t-C₄H₉ 1486 CH₃ 2,3-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1487 CH₃ 2,3-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1488 CH₃ 2,3-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1489 CH₃ 2,3-(CH₃)₂—C₆H₃ Propyn-3-yl 1490 CH₃ 2,3-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1491 CH₃ 2,4-(CH₃)₂—C₆H₃ H 1492 CH₃ 2,4-(CH₃)₂—C₆H₃ CH₃ 1493 CH₃ 2,4-(CH₃)₂—C₆H₃ C₂H₅ 1494 CH₃ 2,4-(CH₃)₂—C₆H₃ n-C₃H₇ 1495 CH₃ 2,4-(CH₃)₂—C₆H₃ i-C₃H₇ 1496 CH₃ 2,4-(CH₃)₂—C₆H₃ n-C₄H₉ 1497 CH₃ 2,4-(CH₃)₂—C₆H₃ t-C₄H₉ 1498 CH₃ 2,4-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1499 CH₃ 2,4-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1500 CH₃ 2,4-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1501 CH₃ 2,4-(CH₃)₂—C₆H₃ Propyn-3-yl 1502 CH₃ 2,4-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1503 CH₃ 2,5-(CH₃)₂—C₆H₃ H 1504 CH₃ 2,5-(CH₃)₂—C₆H₃ CH₃ 1505 CH₃ 2,5-(CH₃)₂—C₆H₃ C₂H₅ 1506 CH₃ 2,5-(CH₃)₂—C₆H₃ n-C₃H₇ 1507 CH₃ 2,5-(CH₃)₂—C₆H₃ i-C₃H₇ 1508 CH₃ 2,5-(CH₃)₂—C₆H₃ n-C₄H₉ 1509 CH₃ 2,5-(CH₃)₂—C₆H₃ t-C₄H₉ 1510 CH₃ 2,5-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1511 CH₃ 2,5-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1512 CH₃ 2,5-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1513 CH₃ 2,5-(CH₃)₂—C₆H₃ Propyn-3-yl 1514 CH₃ 2,5-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1515 CH₃ 2,6-(CH₃)₂—C₆H₃ H 1516 CH₃ 2,6-(CH₃)₂—C₆H₃ CH₃ 1517 CH₃ 2,6-(CH₃)₂—C₆H₃ C₂H₅ 1518 CH₃ 2,6-(CH₃)₂—C₆H₃ n-C₃H₇ 1519 CH₃ 2,6-(CH₃)₂—C₆H₃ i-C₃H₇ 1520 CH₃ 2,6-(CH₃)₂—C₆H₃ n-C₄H₉ 1521 CH₃ 2,6-(CH₃)₂—C₆H₃ t-C₄H₉ 1522 CH₃ 2,6-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1523 CH₃ 2,6-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1524 CH₃ 2,6-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1525 CH₃ 2,6-(CH₃)₂—C₆H₃ Propyn-3-yl 1526 CH₃ 2,6-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1527 CH₃ 3,4-(CH₃)₂—C₆H₃ H 1528 CH₃ 3,4-(CH₃)₂—C₆H₃ CH₃ 1529 CH₃ 3,4-(CH₃)₂—C₆H₃ C₂H₅ 1530 CH₃ 3,4-(CH₃)₂—C₆H₃ n-C₃H₇ 1531 CH₃ 3,4-(CH₃)₂—C₆H₃ i-C₃H₇ 1532 CH₃ 3,4-(CH₃)₂—C₆H₃ n-C₄H₉ 1533 CH₃ 3,4-(CH₃)₂—C₆H₃ t-C₄H₉ 1534 CH₃ 3,4-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1535 CH₃ 3,4-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1536 CH₃ 3,4-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1537 CH₃ 3,4-(CH₃)₂—C₆H₃ Propyn-3-yl 1538 CH₃ 3,4-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1539 CH₃ 3,5-(CH₃)₂—C₆H₃ H 1540 CH₃ 3,5-(CH₃)₂—C₆H₃ CH₃ 1541 CH₃ 3,5-(CH₃)₂—C₆H₃ C₂H₅ 1542 CH₃ 3,5-(CH₃)₂—C₆H₃ n-C₃H₇ 1543 CH₃ 3,5-(CH₃)₂—C₆H₃ i-C₃H₇ 1544 CH₃ 3,5-(CH₃)₂—C₆H₃ n-C₄H₉ 1545 CH₃ 3,5-(CH₃)₂—C₆H₃ t-C₄H₉ 1546 CH₃ 3,5-(CH₃)₂—C₆H₃ n-C₆H₁₃ 1547 CH₃ 3,5-(CH₃)₂—C₆H₃ Prop-1-en-3-yl 1548 CH₃ 3,5-(CH₃)₂—C₆H₃ (E)-1-Chloroprop-1-en-3-yl 1549 CH₃ 3,5-(CH₃)₂—C₆H₃ Propyn-3-yl 1550 CH₃ 3,5-(CH₃)₂—C₆H₃ 3-Methyl-but-2-en-1-yl 1551 CH₃ 2-C₂H₅—C₆H₄ H 1552 CH₃ 2-C₂H₅—C₆H₄ CH₃ 1553 CH₃ 2-C₂H₅—C₆H₄ C₂H₅ 1554 CH₃ 2-C₂H₅—C₆H₄ n-C₃H₇ 1555 CH₃ 2-C₂H₅—C₆H₄ t-C₄H₉ 1556 CH₃ 2-C₂H₅—C₆H₄ n-C₆H₁₃ 1557 CH₃ 2-C₂H₅—C₆H₄ Prop-1-en-3-yl 1558 CH₃ 2-C₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1559 CH₃ 2-C₂H₅—C₆H₄ Propyn-3-yl 1560 CH₃ 2-C₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1561 CH₃ 3-C₂H₅—C₆H₄ H 1562 CH₃ 3-C₂H₅—C₆H₄ CH₃ 1563 CH₃ 3-C₂H₅—C₆H₄ C₂H₅ 1564 CH₃ 3-C₂H₅—C₆H₄ n-C₃H₇ 1565 CH₃ 3-C₂H₅—C₆H₄ i-C₃H₇ 1566 CH₃ 3-C₂H₅—C₆H₄ n-C₄H₉ 1567 CH₃ 3-C₂H₅—C₆H₄ t-C₄H₉ 1568 CH₃ 3-C₂H₅—C₆H₄ n-C₆H₁₃ 1569 CH₃ 3-C₂H₅—C₆H₄ Prop-1-en-3-yl 1570 CH₃ 3-C₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1571 CH₃ 3-C₂H₅—C₆H₄ Propyn-3-yl 1572 CH₃ 3-C₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1573 CH₃ 4-C₂H₅—C₆H₄ H 1574 CH₃ 4-C₂H₅—C₆H₄ CH₃ 1575 CH₃ 4-C₂H₅—C₆H₄ C₂H₅ 1576 CH₃ 4-C₂H₅—C₆H₄ n-C₃H₇ 1577 CH₃ 4-C₂H₅—C₆H₄ i-C₃H₇ 1578 CH₃ 4-C₂H₅—C₆H₄ n-C₄H₉ 1579 CH₃ 4-C₂H₅—C₆H₄ t-C₄H₉ 1580 CH₃ 4-C₂H₅—C₆H₄ n-C₆H₁₃ 1581 CH₃ 4-C₂H₅—C₆H₄ Prop-1-en-3-yl 1582 CH₃ 4-C₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1583 CH₃ 4-C₂H₅—C₆H₄ Propyn-3-yl 1584 CH₃ 4-C₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1585 CH₃ 2-i-C₃H₇—C₆H₄ H 1586 CH₃ 2-i-C₃H₇—C₆H₄ CH₃ 1587 CH₃ 2-i-C₃H₇—C₆H₄ C₂H₅ 1588 CH₃ 2-i-C₃H₇—C₆H₄ n-C₃H₇ 1589 CH₃ 2-i-C₃H₇—C₆H₄ i-C₃H₇ 1590 CH₃ 2-i-C₃H₇—C₆H₄ n-C₄H₉ 1591 CH₃ 2-i-C₃H₇—C₆H₄ t-C₄H₉ 1592 CH₃ 2-i-C₃H₇—C₆H₄ n-C₆H₁₃ 1593 CH₃ 2-i-C₃H₇—C₆H₄ Prop-1-en-3-yl 1594 CH₃ 2-i-C₃H₇—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1595 CH₃ 2-i-C₃H₇—C₆H₄ Propyn-3-yl 1596 CH₃ 2-i-C₃H₇—C₆H₄ 3-Methyl-but-2-en-1-yl 1597 CH₃ 3-i-C₃H₇—C₆H₄ H 1598 CH₃ 3-i-C₃H₇—C₆H₄ CH₃ 1599 CH₃ 3-i-C₃H₇—C₆H₄ C₂H₅ 1600 CH₃ 3-i-C₃H₇—C₆H₄ n-C₃H₇ 1601 CH₃ 3-i-C₃H₇—C₆H₄ i-C₃H₇ 1602 CH₃ 3-i-C₃H₇—C₆H₄ n-C₄H₉ 1603 CH₃ 3-i-C₃H₇—C₆H₄ t-C₄H₉ 1604 CH₃ 3-i-C₃H₇—C₆H₄ n-C₆H₁₃ 1605 CH₃ 3-i-C₃H₇—C₆H₄ Prop-1-en-3-yl 1606 CH₃ 3-i-C₃H₇—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1607 CH₃ 3-i-C₃H₇—C₆H₄ Propyn-3-yl 1608 CH₃ 3-i-C₃H₇—C₆H₄ 3-Methyl-but-2-en-1-yl 1609 CH₃ 4-i-C₃H₇—C₆H₄ H 1610 CH₃ 4-i-C₃H₇—C₆H₄ CH₃ 1611 CH₃ 4-i-C₃H₇—C₆H₄ C₂H₅ 1612 CH₃ 4-i-C₃H₇—C₆H₄ n-C₃H₇ 1613 CH₃ 4-i-C₃H₇—C₆H₄ i-C₃H₇ 1614 CH₃ 4-i-C₃H₇—C₆H₄ n-C₄H₉ 1615 CH₃ 4-i-C₃H₇—C₆H₄ t-C₄H₉ 1616 CH₃ 4-i-C₃H₇—C₆H₄ n-C₆H₁₃ 1617 CH₃ 4-i-C₃H₇—C₆H₄ Prop-1-en-3-yl 1618 CH₃ 4-i-C₃H₇—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1619 CH₃ 4-i-C₃H₇—C₆H₄ Propyn-3-yl 1620 CH₃ 4-i-C₃H₇—C₆H₄ 3-Methyl-but-2-en-1-yl 1621 CH₃ 2-OH—C₆H₄ H 1622 CH₃ 2-OH—C₆H₄ CH₃ 1623 CH₃ 2-OH—C₆H₄ C₂H₅ 1624 CH₃ 2-OH—C₆H₄ n-C₃H₇ 1625 CH₃ 2-OH—C₆H₄ i-C₃H₇ 1626 CH₃ 2-OH—C₆H₄ n-C₄H₉ 1627 CH₃ 2-OH—C₆H₄ t-C₄H₉ 1628 CH₃ 2-OH—C₆H₄ n-C₆H₁₃ 1629 CH₃ 2-OH—C₆H₄ Prop-1-en-3-yl 1630 CH₃ 2-OH—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1631 CH₃ 2-OH—C₆H₄ Propyn-3-yl 1632 CH₃ 2-OH—C₆H₄ 3-Methyl-but-2-en-1-yl 1633 CH₃ 3-OH—C₆H₄ H 1634 CH₃ 3-OH—C₆H₄ CH₃ 1635 CH₃ 3-OH—C₆H₄ C₂H₅ 1636 CH₃ 3-OH—C₆H₄ n-C₃H₇ 1637 CH₃ 3-OH—C₆H₄ i-C₃H₇ 1638 CH₃ 3-OH—C₆H₄ n-C₄H₉ 1639 CH₃ 3-OH—C₆H₄ t-C₄H₉ 1640 CH₃ 3-OH—C₆H₄ n-C₆H₁₃ 1641 CH₃ 3-OH—C₆H₄ Prop-1-en-3-yl 1642 CH₃ 3-OH—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1643 CH₃ 3-OH—C₆H₄ Propyn-3-yl 1644 CH₃ 3-OH—C₆H₄ 3-Methyl-but-2-en-1-yl 1645 CH₃ 4-OH—C₆H₄ H 1646 CH₃ 4-OH—C₆H₄ CH₃ 1647 CH₃ 4-OH—C₆H₄ C₂H₅ 1648 CH₃ 4-OH—C₆H₄ n-C₃H₇ 1649 CH₃ 4-OH—C₆H₄ i-C₃H₇ 1650 CH₃ 4-OH—C₆H₄ n-C₄H₉ 1651 CH₃ 4-OH—C₆H₄ t-C₄H₉ 1652 CH₃ 4-OH—C₆H₄ n-C₆H₁₃ 1653 CH₃ 4-OH—C₆H₄ Prop-1-en-3-yl 1654 CH₃ 4-OH—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1655 CH₃ 4-OH—C₆H₄ Propyn-3-yl 1656 CH₃ 4-OH—C₆H₄ 3-Methyl-but-2-en-1-yl 1657 CH₃ 2-OCH₃—C₆H₄ H 1658 CH₃ 2-OCH₃—C₆H₄ CH₃ 1659 CH₃ 2-OCH₃—C₆H₄ C₂H₅ 1660 CH₃ 2-OCH₃—C₆H₄ n-C₃H₇ 1661 CH₃ 2-OCH₃—C₆H₄ i-C₃H₇ 1662 CH₃ 2-OCH₃—C₆H₄ n-C₄H₉ 1663 CH₃ 2-OCH₃—C₆H₄ t-C₄H₉ 1664 CH₃ 2-OCH₃—C₆H₄ n-C₆H₁₃ 1665 CH₃ 2-OCH₃—C₆H₄ Prop-1-en-3-yl 1666 CH₃ 2-OCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1667 CH₃ 2-OCH₃—C₆H₄ Propyn-3-yl 1668 CH₃ 2-OCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1669 CH₃ 3-OCH₃—C₆H₄ H 1670 CH₃ 3-OCH₃—C₆H₄ CH₃ 1671 CH₃ 3-OCH₃—C₆H₄ C₂H₅ 1672 CH₃ 3-OCH₃—C₆H₄ n-C₃H₇ 1673 CH₃ 3-OCH₃—C₆H₄ i-C₃H₇ 1674 CH₃ 3-OCH₃—C₆H₄ n-C₄H₉ 1675 CH₃ 3-OCH₃—C₆H₄ t-C₄H₉ 1676 CH₃ 3-OCH₃—C₆H₄ n-C₆H₁₃ 1677 CH₃ 3-OCH₃—C₆H₄ Prop-1-en-3-yl 1678 CH₃ 3-OCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1679 CH₃ 3-OCH₃—C₆H₄ Propyn-3-yl 1680 CH₃ 3-OCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1681 CH₃ 4-OCH₃—C₆H₄ H 1682 CH₃ 4-OCH₃—C₆H₄ CH₃ 1683 CH₃ 4-OCH₃—C₆H₄ C₂H₅ 1684 CH₃ 4-OCH₃—C₆H₄ n-C₃H₇ 1685 CH₃ 4-OCH₃—C₆H₄ i-C₃H₇ 1686 CH₃ 4-OCH₃—C₆H₄ n-C₄H₉ 1687 CH₃ 4-OCH₃—C₆H₄ t-C₄H₉ 1668 CH₃ 4-OCH₃—C₆H₄ n-C₆H₁₃ 1689 CH₃ 4-OCH₃—C₆H₄ Prop-1-en-3-yl 1690 CH₃ 4-OCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1691 CH₃ 4-OCH₃—C₆H₄ Propyn-3-yl 1692 CH₃ 4-OCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1693 CH₃ 2-OC₂H₅—C₆H₄ H 1694 CH₃ 2-OC₂H₅—C₆H₄ CH₃ 1695 CH₃ 2-OC₂H₅—C₆H₄ C₂H₅ 1696 CH₃ 2-OC₂H₅—C₆H₄ n-C₃H₇ 1697 CH₃ 2-OC₂H₅—C₆H₄ i-C₃H₇ 1698 CH₃ 2-OC₂H₅—C₆H₄ n-C₄H₉ 1699 CH₃ 2-OC₂H₅—C₆H₄ t-C₄H₉ 1700 CH₃ 2-OC₂H₅—C₆H₄ n-C₆H₁₃ 1701 CH₃ 2-OC₂H₅—C₆H₄ Prop-1-en-3-yl 1702 CH₃ 2-OC₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1703 CH₃ 2-OC₂H₅—C₆H₄ Propyn-3-yl 1704 CH₃ 2-OC₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1705 CH₃ 3-OC₂H₅—C₆H₄ H 1706 CH₃ 3-OC₂H₅—C₆H₄ CH₃ 1707 CH₃ 3-OC₂H₅—C₆H₄ C₂H₅ 1708 CH₃ 3-OC₂H₅—C₆H₄ n-C₃H₇ 1709 CH₃ 3-OC₂H₅—C₆H₄ i-C₃H₇ 1710 CH₃ 3-OC₂H₅—C₆H₄ n-C₄H₉ 1711 CH₃ 3-OC₂H₅—C₆H₄ t-C₄H₉ 1712 CH₃ 3-OC₂H₅—C₆H₄ n-C₆H₁₃ 1713 CH₃ 3-OC₂H₅—C₆H₄ Prop-1-en-3-yl 1714 CH₃ 3-OC₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1715 CH₃ 3-OC₂H₅—C₆H₄ Propyn-3-yl 1716 CH₃ 3-OC₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1717 CH₃ 4-OC₂H₅—C₆H₄ H 1718 CH₃ 4-OC₂H₅—C₆H₄ CH₃ 1719 CH₃ 4-OC₂H₅—C₆H₄ C₂H₅ 1720 CH₃ 4-OC₂H₅—C₆H₄ n-C₃H₇ 1721 CH₃ 4-OC₂H₅—C₆H₄ i-C₃H₇ 1722 CH₃ 4-OC₂H₅—C₆H₄ n-C₄H₉ 1723 CH₃ 4-OC₂H₅—C₆H₄ t-C₄H₉ 1724 CH₃ 4-OC₂H₅—C₆H₄ n-C₆H₁₃ 1725 CH₃ 4-OC₂H₅—C₆H₄ Prop-1-en-3-yl 1726 CH₃ 4-OC₂H₅—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1727 CH₃ 4-OC₂H₅—C₆H₄ Propyn-3-yl 1728 CH₃ 4-OC₂H₅—C₆H₄ 3-Methyl-but-2-en-1-yl 1729 CH₃ 2-O-(i-C₃H₇)—C₆H₄ H 1730 CH₃ 2-O-(i-C₃H₇)—C₆H₄ CH₃ 1731 CH₃ 2-O-(i-C₃H₇)—C₆H₄ C₂H₅ 1732 CH₃ 2-O-(i-C₃H₇)—C₆H₄ n-C₃H₇ 1733 CH₃ 2-O-(i-C₃H₇)—C₆H₄ i-C₃H₇ 1734 CH₃ 2-O-(i-C₃H₇)—C₆H₄ n-C₄H₉ 1735 CH₃ 2-O-(i-C₃H₇)—C₆H₄ t-C₄H₉ 1736 CH₃ 2-O-(i-C₃H₇)—C₆H₄ n-C₆H₁₃ 1737 CH₃ 2-O-(i-C₃H₇)—C₆H₄ Prop-1-en-3-yl 1738 CH₃ 2-O-(i-C₃H₇)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1739 CH₃ 2-O-(i-C₃H₇)—C₆H₄ Propyn-3-yl 1740 CH₃ 2-O-(i-C₃H₇)—C₆H₄ 3-Methyl-but-2-en-1-yl 1741 CH₃ 3-O-(i-C₃H₇)—C₆H₄ H 1742 CH₃ 3-O-(i-C₃H₇)—C₆H₄ CH₃ 1743 CH₃ 3-O-(i-C₃H₇)—C₆H₄ C₂H₅ 1744 CH₃ 3-O-(i-C₃H₇)—C₆H₄ n-C₃H₇ 1745 CH₃ 3-O-(i-C₃H₇)—C₆H₄ i-C₃H₇ 1746 CH₃ 3-O-(i-C₃H₇)—C₆H₄ n-C₄H₉ 1747 CH₃ 3-O-(i-C₃H₇)—C₆H₄ t-C₄H₉ 1748 CH₃ 3-O-(i-C₃H₇)—C₆H₄ n-C₆H₁₃ 1749 CH₃ 3-O-(i-C₃H₇)—C₆H₄ Prop-1-en-3-yl 1750 CH₃ 3-O-(i-C₃H₇)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1751 CH₃ 3-O-(i-C₃H₇)—C₆H₄ Propyn-3-yl 1752 CH₃ 3-O-(i-C₃H₇)—C₆H₄ 3-Methyl-but-2-en-1-yl 1753 CH₃ 4-O-(i-C₃H₇)—C₆H₄ H 1754 CH₃ 4-O-(i-C₃H₇)—C₆H₄ CH₃ 1755 CH₃ 4-O-(i-C₃H₇)—C₆H₄ C₂H₅ 1756 CH₃ 4-O-(i-C₃H₇)—C₆H₄ n-C₃H₇ 1757 CH₃ 4-O-(i-C₃H₇)—C₆H₄ i-C₃H₇ 1758 CH₃ 4-O-(i-C₃H₇)—C₆H₄ n-C₄H₉ 1759 CH₃ 4-O-(i-C₃H₇)—C₆H₄ t-C₄H₉ 1760 CH₃ 4-O-(i-C₃H₇)—C₆H₄ n-C₆H₁₃ 1761 CH₃ 4-O-(i-C₃H₇)—C₆H₄ Prop-1-en-3-yl 1762 CH₃ 4-O-(i-C₃H₇)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1763 CH₃ 4-O-(i-C₃H₇)—C₆H₄ Propyn-3-yl 1764 CH₃ 4-O-(i-C₃H₇)—C₆H₄ 3-Methyl-but-2-en-1-yl 1765 CH₃ 2-O-(t-C₄H₉)—C₆H₄ H 1766 CH₃ 2-O-(t-C₄H₉)—C₆H₄ CH₃ 1767 CH₃ 2-O-(t-C₄H₉)—C₆H₄ C₂H₅ 1768 CH₃ 2-O-(t-C₄H₉)—C₆H₄ n-C₃H₇ 1769 CH₃ 2-O-(t-C₄H₉)—C₆H₄ i-C₃H₇ 1770 CH₃ 2-O-(t-C₄H₉)—C₆H₄ n-C₄H₉ 1771 CH₃ 2-O-(t-C₄H₉)—C₆H₄ t-C₄H₉ 1772 CH₃ 2-O-(t-C₄H₉)—C₆H₄ n-C₆H₁₃ 1773 CH₃ 2-O-(t-C₄H₉)—C₆H₄ Prop-1-en-3-yl 1774 CH₃ 2-O-(t-C₄H₉)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1775 CH₃ 2-O-(t-C₄H₉)—C₆H₄ Propyn-3-yl 1776 CH₃ 2-O-(t-C₄H₉)—C₆H₄ 3-Methyl-but-2-en-1-yl 1777 CH₃ 3-O-(t-C₄H₉)—C₆H₄ H 1778 CH₃ 3-O-(t-C₄H₉)—C₆H₄ CH₃ 1779 CH₃ 3-O-(t-C₄H₉)—C₆H₄ C₂H₅ 1780 CH₃ 3-O-(t-C₄H₉)—C₆H₄ n-C₃H₇ 1781 CH₃ 3-O-(t-C₄H₉)—C₆H₄ i-C₃H₇ 1782 CH₃ 3-O-(t-C₄H₉)—C₆H₄ n-C₄H₉ 1783 CH₃ 3-O-(t-C₄H₉)—C₆H₄ t-C₄H₉ 1784 CH₃ 3-O-(t-C₄H₉)—C₆H₄ n-C₆H₁₃ 1785 CH₃ 3-O-(t-C₄H₉)—C₆H₄ Prop-1-en-3-yl 1786 CH₃ 3-O-(t-C₄H₉)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1787 CH₃ 3-O-(t-C₄H₉)—C₆H₄ Propyn-3-yl 1788 CH₃ 3-O-(t-C₄H₉)—C₆H₄ 3-Methyl-but-2-en-1-yl 1789 CH₃ 4-O-(t-C₄H₉)—C₆H₄ H 1790 CH₃ 4-O-(t-C₄H₉)—C₆H₄ CH₃ 1791 CH₃ 4-O-(t-C₄H₉)—C₆H₄ C₂H₅ 1792 CH₃ 4-O-(t-C₄H₉)—C₆H₄ n-C₃H₇ 1793 CH₃ 4-O-(t-C₄H₉)—C₆H₄ i-C₃H₇ 1794 CH₃ 4-O-(t-C₄H₉)—C₆H₄ n-C₄H₉ 1795 CH₃ 4-O-(t-C₄H₉)—C₆H₄ t-C₄H₉ 1796 CH₃ 4-O-(t-C₄H₉)—C₆H₄ n-C₆H₁₃ 1797 CH₃ 4-O-(t-C₄H₉)—C₆H₄ Prop-1-en-3-yl 1798 CH₃ 4-O-(t-C₄H₉)—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1799 CH₃ 4-O-(t-C₄H₉)—C₆H₄ Propyn-3-yl 1800 CH₃ 4-O-(t-C₄H₉)—C₆H₄ 3-Methyl-but-2-en-1-yl 1801 CH₃ 2-CF₃—C₆H₄ H 1802 CH₃ 2-CF₃—C₆H₄ CH₃ 1803 CH₃ 2-CF₃—C₆H₄ C₂H₅ 1804 CH₃ 2-CF₃—C₆H₄ n-C₃H₇ 1805 CH₃ 2-CF₃—C₆H₄ i-C₃H₇ 1806 CH₃ 2-CF₃—C₆H₄ n-C₄H₉ 1807 CH₃ 2-CF₃—C₆H₄ t-C₄H₉ 1808 CH₃ 2-CF₃—C₆H₄ n-C₆H₁₃ 1809 CH₃ 2-CF₃—C₆H₄ Prop-1-en-3-yl 1810 CH₃ 2-CF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1811 CH₃ 2-CF₃—C₆H₄ Propyn-3-yl 1812 CH₃ 2-CF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1813 CH₃ 3-CF₃—C₆H₄ H 1814 CH₃ 3-CF₃—C₆H₄ CH₃ 1815 CH₃ 3-CF₃—C₆H₄ C₂H₅ 1816 CH₃ 3-CF₃—C₆H₄ n-C₃H₇ 1817 CH₃ 3-CF₃—C₆H₄ i-C₃H₇ 1818 CH₃ 3-CF₃—C₆H₄ n-C₄H₉ 1819 CH₃ 3-CF₃—C₆H₄ t-C₄H₉ 1820 CH₃ 3-CF₃—C₆H₄ n-C₆H₁₃ 1821 CH₃ 3-CF₃—C₆H₄ Prop-1-en-3-yl 1822 CH₃ 3-CF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1823 CH₃ 3-CF₃—C₆H₄ Propyn-3-yl 1824 CH₃ 3-CF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1825 CH₃ 4-CF₃—C₆H₄ H 1826 CH₃ 4-CF₃—C₆H₄ CH₃ 1827 CH₃ 4-CF₃—C₆H₄ C₂H₅ 1828 CH₃ 4-CF₃—C₆H₄ n-C₃H₇ 1829 CH₃ 4-CF₃—C₆H₄ i-C₃H₇ 1830 CH₃ 4-CF₃—C₆H₄ n-C₄H₉ 1831 CH₃ 4-CF₃—C₆H₄ t-C₄H₉ 1832 CH₃ 4-CF₃—C₆H₄ n-C₆H₁₃ 1833 CH₃ 4-CF₃—C₆H₄ Prop-1-en-3-yl 1834 CH₃ 4-CF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1835 CH₃ 4-CF₃—C₆H₄ Propyn-3-yl 1836 CH₃ 4-CF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1837 CH₃ 2-NH₂—C₆H₄ H 1838 CH₃ 2-NH₂—C₆H₄ CH₃ 1839 CH₃ 2-NH₂—C₆H₄ C₂H₅ 1340 CH₃ 2-NH₂—C₆H₄ n-C₃H₇ 1841 CH₃ 2-NH₂—C₆H₄ i-C₃H₇ 1842 CH₃ 2-NH₂—C₆H₄ n-C₄H₉ 1843 CH₃ 2-NH₂—C₆H₄ t-C₄H₉ 1844 CH₃ 2-NH₂—C₆H₄ n-C₆H₁₃ 1845 CH₃ 2-NH₂—C₆H₄ Prop-1-en-3-yl 1846 CH₃ 2-NH₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1847 CH₃ 2-NH₂—C₆H₄ Propyn-3-yl 1848 CH₃ 2-NH₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1849 CH₃ 3-NH₂—C₆H₄ H 1850 CH₃ 3-NH₂—C₆H₄ CH₃ 1851 CH₃ 3-NH₂—C₆H₄ C₂H₅ 1852 CH₃ 3-NH₂—C₆H₄ n-C₃H₇ 1853 CH₃ 3-NH₂—C₆H₄ i-C₃H₇ 1854 CH₃ 3-NH₂—C₆H₄ n-C₄H₉ 1855 CH₃ 3-NH₂—C₆H₄ t-C₄H₉ 1856 CH₃ 3-NH₂—C₆H₄ n-C₆H₁₃ 1857 CH₃ 3-NH₂—C₆H₄ Prop-1-en-3-yl 1858 CH₃ 3-NH₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1859 CH₃ 3-NH₂—C₆H₄ Propyn-3-yl 1860 CH₃ 3-NH₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1861 CH₃ 4-NH₂—C₆H₄ H 1862 CH₃ 4-NH₂—C₆H₄ CH₃ 1863 CH₃ 4-NH₂—C₆H₄ C₂H₅ 1864 CH₃ 4-NH₂—C₆H₄ n-C₃H₇ 1865 CH₃ 4-NH₂—C₆H₄ i-C₃H₇ 1866 CH₃ 4-NH₂—C₆H₄ n-C₄H₉ 1867 CH₃ 4-NH₂—C₆H₄ t-C₄H₉ 1868 CH₃ 4-NH₂—C₆H₄ n-C₆H₁₃ 1869 CH₃ 4-NH₂—C₆H₄ Prop-1-en-3-yl 1870 CH₃ 4-NH₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1871 CH₃ 4-NH₂—C₆H₄ Propyn-3-yl 1872 CH₃ 4-NH₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1873 CH₃ 2-NMe₂—C₆H₄ H 1874 CH₃ 2-NMe₂—C₆H₄ CH₃ 1875 CH₃ 2-NMe₂—C₆H₄ C₂H₅ 1876 CH₃ 2-NMe₂—C₆H₄ n-C₃H₇ 1877 CH₃ 2-NMe₂—C₆H₄ i-C₃H₇ 1878 CH₃ 2-NMe₂—C₆H₄ n-C₄H₉ 1879 CH₃ 2-NMe₂—C₆H₄ t-C₄H₉ 1880 CH₃ 2-NMe₂—C₆H₄ n-C₆H₁₃ 1881 CH₃ 2-NMe₂—C₆H₄ Prop-1-en-3-yl 1882 CH₃ 2-NMe₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1883 CH₃ 2-NMe₂—C₆H₄ Propyn-3-yl 1884 CH₃ 2-NMe₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1885 CH₃ 3-NMe₂—C₆H₄ H 1886 CH₃ 3-NMe₂—C₆H₄ CH₃ 1887 CH₃ 3-NMe₂—C₆H₄ C₂H₅ 1888 CH₃ 3-NMe₂—C₆H₄ n-C₃H₇ 1889 CH₃ 3-NMe₂—C₆H₄ i-C₃H₇ 1890 CH₃ 3-NMe₂—C₆H₄ n-C₄H₉ 1891 CH₃ 3-NMe₂—C₆H₄ t-C₄H₉ 1892 CH₃ 3-NMe₂—C₆H₄ n-C₆H₁₃ 1893 CH₃ 3-NMe₂—C₆H₄ Prop-1-en-3-yl 1894 CH₃ 3-NMe₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1895 CH₃ 3-NMe₂—C₆H₄ Propyn-3-yl 1896 CH₃ 3-NMe₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1897 CH₃ 4-NMe₂—C₆H₄ H 1898 CH₃ 4-NMe₂—C₆H₄ CH₃ 1899 CH₃ 4-NMe₂—C₆H₄ C₂H₅ 1900 CH₃ 4-NMe₂—C₆H₄ n-C₃H₇ 1901 CH₃ 4-NMe₂—C₆H₄ i-C₃H₇ 1902 CH₃ 4-NMe₂—C₆H₄ n-C₄H₉ 1903 CH₃ 4-NMe₂—C₆H₄ t-C₄H₉ 1904 CH₃ 4-NMe₂—C₆H₄ n-C₆H₁₃ 1905 CH₃ 4-NMe₂—C₆H₄ Prop-1-en-3-yl 1906 CH₃ 4-NMe₂—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1907 CH₃ 4-NMe₂—C₆H₄ Propyn-3-yl 1908 CH₃ 4-NMe₂—C₆H₄ 3-Methyl-but-2-en-1-yl 1909 CH₃ 2-Aminothiocarbo- H nyl-C₆H₄ 1910 CH₃ 2-Aminothiocarbo- CH₃ nyl-C₆H₄ 1911 CH₃ 2-Aminothiocarbo- C₂H₅ nyl-C₆H₄ 1912 CH₃ 2-Aminothiocarbo- n-C₃H₇ nyl-C₆H₄ 1913 CH₃ 2-Aminothiocarbo- i-C₃H₇ nyl-C₆H₄ 1914 CH₃ 2-Aminothiocarbo- n-C₄H₉ nyl-C₆H₄ 1915 CH₃ 2-Aminothiocarbo- t-C₄H₉ nyl-C₆H₄ 1916 CH₃ 2-Aminothiocarbo- n-C₆H₁₃ nyl-C₆H₄ 1917 CH₃ 2-Aminothiocarbo- Prop-1-en-3-yl nyl-C₆H₄ 1918 CH₃ 2-Aminothiocarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 1919 CH₃ 2-Aminothiocarbo- Propyn-3-yl nyl-C₆H₄ 1920 CH₃ 2-Aminothiocarbo- 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 1921 CH₃ 3-Aminothiocarbo- H nyl-C₆H₄ 1922 CH₃ 3-Aminothiocarbo- CH₃ nyl-C₆H₄ 1923 CH₃ 3-Aminothiocarbo- C₂H₅ nyl-C₆H₄ 1924 CH₃ 3-Aminothiocarbo- n-C₃H₇ nyl-C₆H₄ 1925 CH₃ 3-Aminothiocarbo- i-C₃H₇ nyl-C₆H₄ 1926 CH₃ 3-Aminothiocarbo- n-C₄H₉ nyl-C₆H₄ 1927 CH₃ 3-Aminothiocarbo- t-C₄H₉ nyl-C₆H₄ 1928 CH₃ 3-Aminothiocarbo- n-C₆H₁₃ nyl-C₆H₄ 1929 CH₃ 3-Aminothiocarbo- Prop-1-en-3-yl nyl-C₆H₄ 1930 CH₃ 3-Aminothiocarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 1931 CH₃ 3-Aminothiocarbo- Propyn-3-yl nyl-C₆H₄ 1932 CH₃ 3-Aminothiocarbo- 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 1933 CH₃ 4-Aminothiocarbo- H nyl-C₆H₄ 1934 CH₃ 4-Aminothiocarbo- CH₃ nyl-C₆H₄ 1935 CH₃ 4-Aminothiocarbo- C₂H₅ nyl-C₆H₄ 1936 CH₃ 4-Aminothiocarbo- n-C₃H₇ nyl-C₆H₄ 1937 CH₃ 4-Aminothiocarbo- i-C₃H₇ nyl-C₆H₄ 1938 CH₃ 4-Aminothiocarbo- n-C₄H₉ nyl-C₆H₄ 1939 CH₃ 4-Aminothiocarbo- t-C₄H₉ nyl-C₆H₄ 1940 CH₃ 4-Aminothiocarbo- n-C₆H₁₃ nyl-C₆H₄ 1941 CH₃ 4-Aminothiocarbo- Prop-1-en-3-yl nyl-C₆H₄ 1942 CH₃ 4-Aminothiocarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 1943 CH₃ 4-Aminothiocarbo- Propyn-3-yl nyl-C₆H₄ 1944 CH₃ 4-Aminothiocarbo- 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 1945 CH₃ 2-OCF₃—C₆H₄ H 1946 CH₃ 2-OCF₃—C₆H₄ CH₃ 1947 CH₃ 2-OCF₃—C₆H₄ C₂H₅ 1948 CH₃ 2-OCF₃—C₆H₄ n-C₃H₇ 1949 CH₃ 2-OCF₃—C₆H₄ i-C₃H₇ 1950 CH₃ 2-OCF₃—C₆H₄ n-C₄H₉ 1951 CH₃ 2-OCF₃—C₆H₄ t-C₄H₉ 1952 CH₃ 2-OCF₃—C₆H₄ n-C₆H₁₃ 1953 CH₃ 2-C₂H₅—C₆H₄ i-C₃H₇ 1954 CH₃ 2-C₂H₅—C₆H₄ n-C₄H₉ 1955 CH₃ 2-OCF₃—C₆H₄ Prop-1-en-3-yl 1956 CH₃ 2-OCF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1957 CH₃ 2-OCF₃—C₆H₄ Propyn-3-yl 1958 CH₃ 2-OCF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1959 CH₃ 3-OCF₃—C₆H₄ H 1960 CH₃ 3-OCF₃—C₆H₄ CH₃ 1961 CH₃ 3-OCF₃—C₆H₄ C₂H₅ 1962 CH₃ 3-OCF₃—C₆H₄ n-C₃H₇ 1963 CH₃ 3-OCF₃—C₆H₄ i-C₃H₇ 1964 CH₃ 3-OCF₃—C₆H₄ n-C₄H₉ 1965 CH₃ 3-OCF₃—C₆H₄ t-C₄H₉ 1966 CH₃ 3-OCF₃—C₆H₄ n-C₆H₁₃ 1967 CH₃ 3-OCF₃—C₆H₄ Prop-1-en-3-yl 1968 CH₃ 3-OCF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1969 CH₃ 3-OCF₃—C₆H₄ Propyn-3-yl 1970 CH₃ 3-OCF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1971 CH₃ 4-OCF₃—C₆H₄ H 1972 CH₃ 4-OCF₃—C₆H₄ CH₃ 1973 CH₃ 4-OCF₃—C₆H₄ C₂H₅ 1974 CH₃ 4-OCF₃—C₆H₄ n-C₃H₇ 1975 CH₃ 4-OCF₃—C₆H₄ i-C₃H₇ 1976 CH₃ 4-OCF₃—C₆H₄ n-C₄H₉ 1977 CH₃ 4-OCF₃—C₆H₄ t-C₄H₉ 1978 CH₃ 4-OCF₃—C₆H₄ n-C₆H₁₃ 1979 CH₃ 4-OCF₃—C₆H₄ Prop-1-en-3-yl 1980 CH₃ 4-OCF₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1981 CH₃ 4-OCF₃—C₆H₄ Propyn-3-yl 1982 CH₃ 4-OCF₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1983 CH₃ 2-SCH₃—C₆H₄ H 1984 CH₃ 2-SCH₃—C₆H₄ CH₃ 1985 CH₃ 2-SCH₃—C₆H₄ C₂H₅ 1986 CH₃ 2-SCH₃—C₆H₄ n-C₃H₇ 1987 CH₃ 2-SCH₃—C₆H₄ i-C₃H₇ 1988 CH₃ 2-SCH₃—C₆H₄ n-C₄H₉ 1989 CH₃ 2-SCH₃—C₆H₄ t-C₄H₉ 1990 CH₃ 2-SCH₃—C₆H₄ n-C₆H₁₃ 1991 CH₃ 2-SCH₃—C₆H₄ Prop-1-en-3-yl 1992 CH₃ 2-SCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 1993 CH₃ 2-SCH₃—C₆H₄ Propyn-3-yl 1994 CH₃ 2-SCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 1995 CH₃ 3-SCH₃—C₆H₄ H 1996 CH₃ 3-SCH₃—C₆H₄ CH₃ 1997 CH₃ 3-SCH₃—C₆H₄ C₂H₅ 1998 CH₃ 3-SCH₃—C₆H₄ n-C₃H₇ 1999 CH₃ 3-SCH₃—C₆H₄ i-C₃H₇ 2000 CH₃ 3-SCH₃—C₆H₄ n-C₄H₉ 2001 CH₃ 3-SCH₃—C₆H₄ t-C₄H₉ 2002 CH₃ 3-SCH₃—C₆H₄ n-C₆H₁₃ 2003 CH₃ 3-SCH₃—C₆H₄ Prop-1-en-3-yl 2004 CH₃ 3-SCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 2005 CH₃ 3-SCH₃—C₆H₄ Propyn-3-yl 2006 CH₃ 3-SCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 2007 CH₃ 4-SCH₃—C₆H₄ H 2008 CH₃ 4-SCH₃—C₆H₄ CH₃ 2009 CH₃ 4-SCH₃—C₆H₄ C₂H₅ 2010 CH₃ 4-SCH₃—C₆H₄ n-C₃H₇ 2011 CH₃ 4-SCH₃—C₆H₄ i-C₃H₇ 2012 CH₃ 4-SCH₃—C₆H₄ n-C₄H₉ 2013 CH₃ 4-SCH₃—C₆H₄ t-C₄H₉ 2014 CH₃ 4-SCH₃—C₆H₄ n-C₆H₁₃ 2015 CH₃ 4-SCH₃—C₆H₄ Prop-1-en-3-yl 2016 CH₃ 4-SCH₃—C₆H₄ (E)-1-Chloroprop-1-en-3-yl 2017 CH₃ 4-SCH₃—C₆H₄ Propyn-3-yl 2018 CH₃ 4-SCH₃—C₆H₄ 3-Methyl-but-2-en-1-yl 2019 CH₃ 2-Methyl- H sulfonyl-C₆H₄ 2020 CH₃ 2-Methyl- CH₃ sulfonyl-C₆H₄ 2021 CH₃ 2-Methyl- C₂H₅ sulfonyl-C₆H₄ 2022 CH₃ 2-Methyl- n-C₃H₇ sulfonyl-C₆H₄ 2023 CH₃ 2-Methyl- i-C₃H₇ sulfonyl-C₆H₄ 2024 CH₃ 2-Methyl- n-C₄H₉ sulfonyl-C₆H₄ 2025 CH₃ 2-Methyl- t-C₄H₉ sulfonyl-C₆H₄ 2026 CH₃ 2-Methyl- n-C₆H₁₃ sulfonyl-C₆H₄ 2027 CH₃ 2-Methyl- Prop-1-en-3-yl sulfonyl-C₆H₄ 2028 CH₃ 2-Methyl- (E)-1-Chloroprop-1-en-3-yl sulfonyl-C₆H₄ 2029 CH₃ 2-Methyl- Propyn-3-yl sulfonyl-C₆H₄ 2030 CH₃ 2-Methyl- 3-Methyl-but-2-en-1-yl sul fonyl-C₆H₄ 2031 CH₃ 3-Methyl- H sulfonyl-C₆H₄ 2032 CH₃ 3-Methyl- CH₃ sulfonyl-C₆H₄ 2033 CH₃ 3-Methyl- C₂H₅ sulfonyl-C₆H₄ 2034 CH₃ 3-Methyl- n-C₃H₇ sulfonyl-C₆H₄ 2035 CH₃ 3-Methyl- i-C₃H₇ sulfonyl-C₆H₄ 2036 CH₃ 3-Methyl- n-C₄H₉ sulfonyl-C₆H₄ 2037 CH₃ 3-Methyl- t-C₄H₉ sulfonyl-C₆H₄ 2038 CH₃ 3-Methyl- n-C₆H₁₃ sulfonyl-C₆H₄ 2039 CH₃ 3-Methyl- Prop-1-en-3-yl sulfonyl-C₆H₄ 2040 CH₃ 3-Methyl- (E)-1-Chloroprop-1-en-3-yl sulfonyl-C₆H₄ 2041 CH₃ 3-Methyl- Propyn-3-yl sulfonyl-C₆H₄ 2042 CH₃ 3-Methyl- 3-Methyl-but-2-en-1-yl sulfonyl-C₆H₄ 2043 CH₃ 4-Methyl- H sulfonyl-C₆H₄ 2044 CH₃ 4-Methyl- CH₃ sulfonyl-C₆H₄ 2045 CH₃ 4-Methyl- C₂H₅ sulfonyl-C₆H₄ 2046 CH₃ 4-Methyl- n-C₃H₇ sulfonyl-C₆H₄ 2047 CH₃ 4-Methyl- i-C₃H₇ sulfonyl-C₆H₄ 2048 CH₃ 4-Methyl- n-C₄H₉ sulfonyl-C₆H₄ 2049 CH₃ 4-Methyl- t-C₄H₉ sulfonyl-C₆H₄ 2050 CH₃ 4-Methyl- n-C₆H₁₃ sulfonyl-C₆H₄ 2051 CH₃ 4-Methyl- Prop-1-en-3-yl sulfonyl-C₆H₄ 2052 CH₃ 4-Methyl- (E)-1-Chloroprop-1-en-3-yl sulfonyl-C₆H₄ 2053 CH₃ 4-Methyl- Propyn-3-yl sulfonyl-C₆H₄ 2054 CH₃ 4-Methyl- 3-Methyl-but-2-en-1-yl sulfonyl-C₆H₄ 2055 CH₃ 2-Methoxycarbo- H nyl-C₆H₄ 2056 CH₃ 2-Methoxycarbo- CH₃ nyl-C₆H₄ 2057 CH₃ 2-Methoxycarbo- C₂H₅ nyl-C₆H₄ 2058 CH₃ 2-Methoxycarbo- n-C₃H₇ nyl-C₆H₄ 2059 CH₃ 2-Methoxycarbo- i-C₃H₇ nyl-C₆H₄ 2060 CH₃ 2-Methoxycarbo- n-C₄H₉ nyl-C₆H₄ 2061 CH₃ 2-Methoxycarbo- t-C₄H₉ nyl-C₆H₄ 2062 CH₃ 2-Methoxycarbo- n-C₆H₁₃ nyl-C₆H₄ 2063 CH₃ 2-Methoxycarbo- Prop-1-en-3-yl nyl-C₆H₄ 2064 CH₃ 2-Methoxycarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 2065 CH₃ 2-Methoxycarbo- Propyn-3-yl nyl-C₆H₄ 2066 CH₃ 2-Methoxycarbo- 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 2067 CH₃ 3-Methoxycarbo- H nyl-C₆H₄ 2068 CH₃ 3-Methoxycarbo- CH₃ nyl-C₆H₄ 2069 CH₃ 3-Methoxycarbo- C₂H₅ nyl-C₆H₄ 2070 CH₃ 3-Methoxycarbo- n-C₃H₇ nyl-C₆H₄ 2071 CH₃ 3-Methoxycarbo- i-C₃H₇ nyl-C₆H₄ 2072 CH₃ 3-Methoxycarbo- n-C₄H₉ nyl-C₆H₄ 2073 CH₃ 3-Methoxycarbo- t-C₄H₉ nyl-C₆H₄ 2074 CH₃ 3-Methoxycarbo- n-C₆H₁₃ nyl-C₆H₄ 2075 CH₃ 3-Methoxycarbo- Prop-1-en-3-yl nyl-C₆H₄ 2076 CH₃ 3-Methoxycarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 2077 CH₃ 3-Methoxycarbo- Propyn-3-yl nyl-C₆H₄ 2078 CH₃ 3-Methoxycarbo 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 2079 CH₃ 4-Methoxycarbo- H nyl-C₆H₄ 2080 CH₃ 4-Methoxycarbo- CH₃ nyl-C₆H₄ 2081 CH₃ 4-Methoxycarbo- C₂H₅ nyl-C₆H₄ 2082 CH₃ 4-Methoxycarbo- n-C₃H₇ nyl-C₆H₄ 2083 CH₃ 4-Methoxycarbo- i-C₃H₇ nyl-C₆H₄ 2084 CH₃ 4-Methoxycarbo- n-C₄H₉ nyl-C₆H₄ 2085 CH₃ 4-Methoxycarbo- t-C₄H₉ nyl-C₆H₄ 2086 CH₃ 4-Methoxycarbo- n-C₆H₁₃ nyl-C₆H₄ 2087 CH₃ 4-Methoxycarbo- Prop-1-en-3-yl nyl-C₆H₄ 2088 CH₃ 4-Methoxycarbo- (E)-1-Chloroprop-1-en-3-yl nyl-C₆H₄ 2089 CH₃ 4-Methoxycarbo- Propyn-3-yl nyl-C₆H₄ 2090 CH₃ 4-Methoxycarbo- 3-Methyl-but-2-en-1-yl nyl-C₆H₄ 2091 CH₃ 2-Ethoxy- H carbonyl-C₆H₄ 2092 CH₃ 2-Ethoxy- CH₃ carbonyl-C₆H₄ 2093 CH₃ 2-Ethoxy- C₂H₅ carbonyl-C₆H₄ 2094 CH₃ 2-Ethoxy- n-C₃H₇ carbonyl-C₆H₄ 2095 CH₃ 2-Ethoxy- i-C₃H₇ carbonl-C₆H₄ 2096 CH₃ 2-Ethoxy- n-C₄H₉ carbonyl-C₆H₄ 2097 CH₃ 2-Ethoxy- t-C₄H₉ carbonyl-C₆H₄ 2098 CH₃ 2-Ethoxy- n-C₆H₁₃ carbonyl-C₆H₄ 2099 CH₃ 2-Ethoxy- Prop-1-en-3-yl carbonyl-C₆H₄ 2100 CH₃ 2-Ethoxy- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2101 CH₃ 2-Ethoxy- Propyn-3-yl carbonyl-C₆H₄ 2102 CH₃ 2-Ethoxy- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2103 CH₃ 3-Ethoxy- H carbonyl-C₆H₄ 2104 CH₃ 3-Ethoxy- CH₃ carbonyl-C₆H₄ 2105 CH₃ 3-Ethoxy- C₂H₅ carbonyl-C₆H₄ 2106 CH₃ 3-Ethoxy- n-C₃H₇ carbonyl-C₆H₄ 2107 CH₃ 3-Ethoxy- i-C₃H₇ carbonyl-C₆H₄ 2108 CH₃ 3-Ethoxy- n-C₄H₉ carbonyl-C₆H₄ 2109 CH₃ 3-Ethoxy- t-C₄H₉ carbonyl-C₆H₄ 2110 CH₃ 3-Ethoxy- n-C₆H₁₃ carbonyl-C₆H₄ 2111 CH₃ 3-Ethoxy- Prop-1-en-3-yl carbonyl-C₆H₄ 2112 CH₃ 3-Ethoxy- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2113 CH₃ 3-Ethoxy- Propyn-3-yl carbonyl-C₆H₄ 2114 CH₃ 3-Ethoxy- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2115 CH₃ 4-Ethoxy- H carbonyl-C₆H₄ 2116 CH₃ 4-Ethoxy- CH₃ carbonyl-C₆H₄ 2117 CH₃ 4-Ethoxy- C₂H₅ carbonyl-C₆H₄ 2118 CH₃ 4-Ethoxy- n-C₃H₇ carbonyl-C₆H₄ 2119 CH₃ 4-Ethoxy- i-C₃H₇ carbonyl-C₆H₄ 2120 CH₃ 4-Ethoxy- n-C₄H₉ carbonyl-C₆H₄ 2121 CH₃ 4-Ethoxy- t-C₄H₉ carbonyl-C₆H₄ 2122 CH₃ 4-Ethoxy- n-C₆H₁₃ carbonyl-C₆H₄ 2123 CH₃ 4-Ethoxy- Prop-1-en-3-yl carbonyl-C₆H₄ 2124 CH₃ 4-Ethoxy- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2125 CH₃ 4-Ethoxy- Propyn-3-yl carbonyl-C₆H₄ 2126 CH₃ 4-Ethoxy- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2127 CH₃ 2-Amino- H carbonyl-C₆H₄ 2128 CH₃ 2-Amino- CH₃ carbonyl-C₆H₄ 2129 CH₃ 2-Amino- C₂H₅ carbonyl-C₆H₄ 2130 CH₃ 2-Amino- n-C₃H₇ carbonyl-C₆H₄ 2131 CH₃ 2-Amino- i-C₃H₇ carbonyl-C₆H₄ 2132 CH₃ 2-Amino- n-C₄H₉ carbonyl-C₆H₄ 2133 cH3 2-Amino- t-C₄H₉ carbonyl-C₆H₄ 2134 CH₃ 2-Amino- n-C₆H₁₃ carbonyl-C₆H₄ 2135 CH₃ 2-Amino- Prop-1-en-3-yl carbonyl-C₆H₄ 2136 CH₃ 2-Amino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2137 CH₃ 2-Amino- Propyn-3-yl carbonyl-C₆H₄ 2138 CH₃ 2-Amino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2139 CH₃ 3-Amino- H carbonyl-C₆H₄ 2140 CH₃ 3-Amino- CH₃ carbonyl-C₆H₄ 2141 CH₃ 3-Amino- C₂H₅ carbonyl-C₆H₄ 2142 CH₃ 3-Amino- n-C₃H₇ carbonyl-C₆H₄ 2143 CH₃ 3-Amino- i-C₃H₇ carbonyl-C₆H₄ 2144 CH₃ 3-Amino- n-C₄H₉ carbonyl-C₆H₄ 2145 CH₃ 3-Amino- t-C₄H₉ carbonyl-C₆H₄ 2146 CH₃ 3-Amino- n-C₆H₁₃ carbonyl-C₆H₄ 2147 CH₃ 3-Amino- Prop-1-en-3-yl carbonyl-C₆H₄ 2148 CH₃ 3-Amino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2149 CH₃ 3-Amino- Propyn-3-yl carbonyl-C₆H₄ 2150 CH₃ 3-Amino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2151 CH₃ 4-Amino- H carbonyl-C₆H₄ 2152 CH₃ 4-Amino- CH₃ carbonyl-C₆H₄ 2153 CH₃ 4-Amino- C₂H₅ carbonyl-C₆H₄ 2154 CH₃ 4-Amino- n-C₃H₇ carbonyl-C₆H₄ 2155 CH₃ 4-Amino- i-C₃H₇ carbonyl-C₆H₄ 2156 CH₃ 4-Amino- n-C₄H₉ carbonyl-C₆H₄ 2157 CH₃ 4-Amino- t-C₄H₉ carbonyl-C₆H₄ 2158 CH₃ 4-Amino- n-C₆H₁₃ carbonyl-C₆H₄ 2159 CH₃ 4-Amino- Prop-1-en-3-yl carbonyl-C₆H₄ 2160 CH₃ 4-Amino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2161 CH₃ 4-Amino- Propyn-3-yl carbonyl-C₆H₄ 2162 CH₃ 4-Amino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2163 CH₃ 2-(N-Methylamino- H carbonyl)-C₆H₄ 2164 CH₃ 2-(N-Methylamino- CH₃ carbonyl)-C₆H₄ 2165 CH₃ 2-(N-Methylamino- C₂H₅ carbonyl)-C₆H₄ 2166 CH₃ 2-(N-Methylamino- n-C₃H₇ carbonyl)-C₆H₄ 2167 CH₃ 2-(N-Methylamino- i-C₃H₇ carbonyl)-C₆H₄ 2168 CH₃ 2-(N-Methylamino- n-C₄H₉ carbonyl)-C₆H₄ 2169 CH₃ 2-(N-Methylamino- t-C₄H₉ carbonyl)-C₆H₄ 2170 CH₃ 2-(N-Methylamino- n-C₆H₁₃ carbonyl)-C₆H₄ 2171 CH₃ 2-(N-Methylamino- Prop-1-en-3-yl carbonyl)-C₆H₄ 2172 CH₃ 2-(N-Methylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl)-C₆H₄ 2173 CH₃ 2-(N-Methylamino- Propyn-3-yl carbonyl)-C₆H₄ 2174 CH₃ 2-(N-Methylamino- 3-Methyl-but-2-en-1-yl carbonyl)-C₆H₄ 2175 CH₃ 3-(N-Methylanino- H carbonyl)-C₆H₄ 2176 CH₃ 3-(N-Methylamino- CH₃ carbonyl)-C₆H₄ 2177 CH₃ 3-(N-Methylamino- C₂H₅ carbonyl)-C₆H₄ 2178 CH₃ 3-(N-Methylamino- n-C₃H₇ carbonyl)-C₆H₄ 2179 CH₃ 3-(N-Methylamino- i-C₃H₇ carbonyl)-C₆H₄ 2180 CH₃ 3-(N-Methylamino- n-C₄H₉ carbonyl)-C₆H₄ 2181 CH₃ 3-(N-Methylamino- t-C₄H₉ carbonyl)-C₆H₄ 2182 CH₃ 3-(N-Methylamino- n-C₆H₁₃ carbonyl)-C₆H₄ 2183 CH₃ 3-(N-Methylamino- Prop-1-en-3-yl carbonyl)-C₆H₄ 2184 CH₃ 3-(N-Methylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl)-C₆H₄ 2185 CH₃ 3-(N-Methylamino- Propyn-3-yl carbonyl)-C₆H₄ 2186 CH₃ 3-(N-Methylamino- 3-Methyl-but-2-en-1-yl carbonyl)-C₆H₄ 2187 CH₃ 4-(N-Methylamino- H carbonyl)-C₆H₄ 2188 CH₃ 4-(N-Methylamino- CH₃ carbonyl)-C₆H₄ 2189 CH₃ 4-(N-Methylamino- C₂H₅ carbonyl)-C₆H₄ 2190 CH₃ 4-(N-Methylamino- n-C₃H₇ carbonyl)-C₆H₄ 2191 CH₃ 4-(N-Methylamino- i-C₃H₇ carbonyl)-C₆H₄ 2192 CH₃ 4-(N-Methylamino- n-C₄H₉ carbonyl)-C₆H₄ 2193 CH₃ 4-(N-Methylamino- t-C₄H₉ carbonyl)-C₆H₄ 2194 CH₃ 4-(N-Methylamino- n-C₆H₁₃ carbonyl)-C₆H₄ 2195 CH₃ 4-(N-Methylamino- Prop-1-en-3-yl carbonyl)-C₆H₄ 2196 CH₃ 4-(N-Methylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl)-C₆H₄ 2197 CH₃ 4-(N-Methylamino- Propyn-3-yl carbonyl)-C₆H₄ 2198 CH₃ 4-(N-Methylamino- 3-Methyl-but-2-en-1-yl carbonyl)-C₆H₄ 2199 CH₃ 2-Dimethylamino- H carbonyl-C₆H₄ 2200 CH₃ 2-Dimethylamino- CH₃ carbonyl-C₆H₄ 2201 CH₃ 2-Dimethylamino- C₂H₅ carbonyl-C₆H₄ 2202 CH₃ 2-Dimethylamino- n-C₃H₇ carbonyl-C₆H₄ 2203 CH₃ 2-Dimethylamino- i-C₃H₇ carbonyl-C₆H₄— 2204 CH₃ 2-Dimethylamino- n-C₄H₉ carbonyl-C₆H₄ 2205 CH₃ 2-Dimethylamino- t-C₄H₉ carbonyl-C₆H₄ 2206 CH₃ 2-Dimethylamino- n-C₆H₁₃ carbonyl-C₆H₄ 2207 CH₃ 2-Dimethylamino- Prop-1-en-3-yl carbonyl-C₆H₄ 2208 CH₃ 2-Dimethylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2209 CH₃ 2-Dimethylamino- Propyn-3-yl carbonyl-C₆H₄ 2210 CH₃ 2-Dimethylamino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2211 CH₃ 3-Dimethylamino- H carbonyl-C₆H₄ 2212 CH₃ 3-Dimethylamino- CH₃ carbonyl-C₆H₄ 2213 CH₃ 3-Dimethylamino- C₂H₅ carbonyl-C₆H₄ 2214 CH₃ 3-Dimethylamino- n-C₃H₇ carbonyl-C₆H₄ 2215 CH₃ 3-Dimethylamino- i-C₃H₇ carbonyl-C₆H₄ 2216 CH₃ 3-Dimethylamino- n-C₄H₉ carbonyl-C₆H₄ 2217 CH₃ 3-Dimethylamino- t-C₄H₉ carbonyl-C₆H₄ 2218 CH₃ 3-Dimethylamino- n-C₆H₁₃ carbonyl-C₆H₄ 2219 CH₃ 3-Dimethylamino- Prop-1-en-3-yl carbonyl-C₆H₄ 2220 CH₃ 3-Dimethylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2221 CH₃ 3-Dimethylamino- Propyn-3-yl carbonyl-C₆H₄ 2222 CH₃ 3-Dimethylamino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄ 2223 CH₃ 4-Dimethylamino- H carbonyl-C₆H₄ 2224 CH₃ 4-Dimethylamino- CH₃ carbonyl-C₆H₄ 2225 CH₃ 4-Dimethylamino- C₂H₅ carbonyl-C₆H₄ 2226 CH₃ 4-Dimethylamino- n-C₃H₇ carbonyl-C₆H₄ 2227 CH₃ 4-Dimethylamino- i-C₃H₇ carbonyl-C₆H₄ 2228 CH₃ 4-Dimethylamino- n-C₄H₉ carbonyl-C₆H₄ 2229 CH₃ 4-Dimethylamino- t-C₄H₉ carbonyl-C₆H₄ 2230 CH₃ 4-Dimethylamino- n-C₆H₁₃ carbonyl-C₆H₄ 2231 CH₃ 4-Dimethylamino- Prop-1-en-3-yl carbonyl-C₆H₄ 2232 CH₃ 4-Dimethylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl-C₆H₄ 2233 CH₃ 4-Dimethylamino- Propyn-3-yl carbonyl-C₆H₄ 2234 CH₃ 4-Dimethylamino- 3-Methyl-but-2-en-1-yl carbonyl-C₆H₄

The compounds I are suitable as fungicides.

The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes and Basidiomycetes. They are systemically active in some cases and can be employed as foliar and soil fungicides.

They are of particular importance for the control of a multiplicity of fungi on various crop plants such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugar cane, grapes, fruit and decorative plants and vegetable plants such as cucumbers, beans and cucurbits, and on the seeds of these plants.

They are specifically suitable for the control of the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurb its, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.

The compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected from fungal attack with a fungicidally effective amount of the active compounds. They are applied before or after the infection of the materials, plants or seeds by the fungi.

They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; it should in any case guarantee a fine and uniform dispersion of the ortho-substituted benzyl ester of a cyclopropanecarbonic acid. The formulations are prepared in a known manner, eg. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents when water is used as a diluent. Suitable auxiliary substances for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silicic acid, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

The fungicidal compositions in general contain from 0.1 to 95, preferably from 0.5 to 90, % by weight of active compound.

Depending on the type of effect desired, the application rates are from 0.01 to 2.0 kg of active compound per ha.

In seed treatment, active compound amounts of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed are in general needed.

The compositions according to the invention can also be present in the application form as fungicides together with other active compounds, the eg. with herbicides, insecticides, growth regulators, fungicides or alternatively with fertilizers.

On mixing with fungicides, in many cases an increase in the fungicidal spectrum of action is obtained here.

The following list of fungicides with which the compounds according to the invention can be applied together is intended to illustrate the combination possibilities, but not restrict them:

sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-mercapto-1-oxide, 3-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diyl-bis(1-(2,2,2-trichloroethyl))formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl)-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thio-ureido)benzene,

and also various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoyl alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl-(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione 3-(3,5-dichloropheyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylamiocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichloropheyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazoyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are additionally suitable for controlling pests from the class of insects, arachnids and nematodes effectively. They can be employed as pesticides in plant protection and in the hygiene, stored products protection and veterinary sectors.

The harmful insects include from the order of the butterflies (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.

From the order of the dipterous insects (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina [sic], Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterous insects (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.

From the order of the bed bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the plant-sucking insects (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

From the order of the orthopterous insects (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus. maroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example spiders (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.

From the class of the nematodes, for example, root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifoiji, stem and leaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.

The active compounds can be applied as such or in the form of their formulations or the application forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering compositions or granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes of use; they should in any case as far as possible guarantee the finest dispersion of the active compounds according to the invention.

The active compound concentrations in the ready-for-application preparations can be varied within quite substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active compounds can also be used with great success in ultra-low volume processes (ULV), where it is possible to apply formulations containing more than 95% by weight of active compound or even the active compound without additives.

The application rate of active compound for controlling pests under outdoor conditions is from 0.1 to 2.0, preferably from 0.2 to 1.0 kg/ha.

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, and also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water are suitable.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which are suitable for dilution with water.

Suitable surface-active substances are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Powders, scattering compositions and dusts can be prepared by mixing or joint grinding of the active substances with a solid carrier.

The formulations in general contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed here in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. A dust which contains 5% by weight of the active compound is obtained in this way.

II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed on the surface of this silica gel. A preparation of the active compound having good adhesion is obtained in this way (active compound content 23% by weight).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 9% by weight).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16% by weight).

V. 80 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and the mixture is ground in a hammer mill (active compound content 80% by weight).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for application in the form of very small drops (active compound content 90% by weight).

VII. 20 parts by weight of a compound No. 11 according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

VIII. 20 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active compound.

Granules, eg. coated, impregnated and homogeneous granules, can be produced by binding the active compounds to solid carriers. Solid carriers are eg. mineral earths, such as silica gel, asilicic acids, silica gels silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nut shell meal, cellulose powder and other solid carriers.

Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if appropriate even only immediately before application (tank mix). These agents can be admixed to the compositions according to the invention in the weight ratio 1:10-10:1.

SYNTHESIS EXAMPLES

The procedures presented in the synthesis examples below were utilized with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are shown in the following tables with physical data.

Example 1

Preparation of methyl (E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-acetyl)iminooxymethyl]phenylacetate

21 g (0.21 mol) of diacetyl monoxime are added under protective gas and with slight cooling at room temperature to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide and the mixture is stirred for 30 min at room temperature. A solution of 60 g (0.21 mol) of methyl 2-methoxyimino-2-(2′bromomethyl)phenylacetate in 360 ml of dimethylformamide is then added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na₂SO₄ and concentrated. The residue is suspended in a little cold methanol. After filtering off with suction, 38 g (59%) of the title compound are obtained as light brown crystals having a melting point of 69-71° C.

¹H-NMR (CDCl₃):δ=1.87(s,3H); 2.30(s,3H); 3.85(s,3H); 4.05(s,3H); 5.15(s,2H); 7.17-7.48(m,4H) ppm.

Example 2

Preparation of methyl (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-ethoxyiminoethyl))iminooxymethyl]phenylacetate

0.96 g (9.8 mmol) of O-ethylhydroxylamine hydrochloride and 0.6 g of dry molecular sieve beads (3 A) are added to a solution of 2.5 g (8.2 mmol) of methyl (E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-acetyl)iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is allowed to stand at room temperature for 5 days. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na₂SO₄ and concentrated. After triturating the residue with n-hexane and filtering off with suction, 1.8 g (63%) of the title compound are obtained as pale yellow crystals having a melting point of 69-72° C.

¹H-NMR (CDCl₃):δ=1.27(t,3H); 1.96(s,3H); 1.99(s,3H); 3.84(s,3H); 4.04(s,3H); 4.17(q,2H); 5.06(s,2H); 7.17-7.49(m,4H) ppm

Example 3

Preparation of (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-ethoxyiminoethyl))iminooxymethyl]phenylacetic acid monomethylamide

0.90 g (2.60 mmol) of methyl (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl,1″-(1″′-ethoxyiminoethyl))iminooxymethyl]-phenylacetate is dissolved in 50 ml of tetrahydrofuran, treated with 2.0 g of 40% strength aqueous monomethylamine solution and stirred et room temperature for 16 h. The mixture is then treated with water and extracted with methyl tert-butyl ether, and the organic phase is washed with water, dried over Na₂SO₄ and concentrated on a rotary evaporator. As a residue, 0.80 g (89%) of the title compound remains as a pale yellow oil.

¹H-NMR (CDCl₃):δ=1.28(t,3H); 1.97(s,3H); 1.99(s,3H); 2.90(d,3H); 3.96(s,3H); 4.18(q,2H); 5.07(s,2H); 6.74(br,1H);7.17-7.48(m,4H) ppm.

Example 4

Preparation of 4-hydroxyimino-2,2-dimethylpentan-3-one

A solution of 40 g of hydrogen chloride in 156 g of diethyl ether is added dropwise at room temperature to 96 g (0.84 mol) of 2,2-dimethyl-3-pentanone in 960 g of toluene. After cooling to −10° C., a solution of 95 g of n-butyl nitrite in 470 g of diethyl ether is added dropwise. The mixture is stirred at from −10° C. to 0° C. for 4 hours and then allowed to come to room temperature. After a total of 16 h, the reaction mixture is washed three times with 1 l of ice-water each time and then extracted twice with 1 l of 1M sodium hydroxide solution each time. The alkaline phase is separated off and neutralized with 20% strength sulfuric acid. The crude product is filtered off with suction and, after drying, recrystallized from n-hexane. 66 g (55%) of the title compound are obtained as a pale yellow powder of melting point 107-110° C.

¹H-NMR (CDCl₃):δ=1.29(s,9H); 1.99(s,3H); 8.30(s,1H) ppm.

Example 5

Preparation of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′,1″′-dimethylethylcarbonyl))iminooxymethyl]phenylacetate

25 g (0.17 mol) of 4-hydroxyimino-2,2-dimethylpentan-3-one are added in portions under protective gas to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide, the reaction mixture warming to 50° C. stirring is continued for 30 min, then a solution of 50 g (0.17 mol) of methyl 2-methoxyimino-2-(2′-bromomethyl)phenylacetate in 300 ml of dimethylformamide is added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na₂SO₂ [sic] and concentrated. The black oily residue is purified by column chromatography on silica gel (methyl tert-butyl ether/n-hexane) and the tube crude product thus obtained is suspended in ice-cold methanol. After filtering off with suction, 24 g (41%) of the title compound are obtained as an almost colorless powder of melting point 58-62° C.

¹H-NMR (CDCl₃):δ=1.19(s,9H); 1.90(s,3H); 3.83(s,3H); 4.04(s,3H); 5.11(s,2H); 7.18-7.45(m,4H) ppm.

Example 6

Preparation of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl))iminooxymethyl]phenylacetate

5.9 g (26 mmol) of O-6-(4′-chlorophenyl)hexylhydroxylamine, 3.6 g of dry molecular sieve beads (3 A) and 1.6 g (8.6 mmol) of p-toluenesulfonic acid hydrate are added to a solution of 3.0 g (8.6 mmol) of methyl (E)-2-methoxyimino-2-[2′-(1″- methyl, 1″-(1″′, 1″′-dimethylethylcarbonyl))iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is refluxed for 3 h. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na₂SO₄ and concentrated. After column chromatography on silica gel (hexane/methyl tert-butyl ether), 3.8 g (79%) of the title compound are obtained as a pale yellow oil.

¹H-NMR (CDCl₃):δ=1.09(s,9H); 1.26-1.42(m,4H); 1.52-1.67(m,4H); 1.90(s,3H); 2.57(t,2H); 3.84(s,3H); 3.99(t,2H); 4.03(s,3H); 5.02(s,2H); 7.07-7.47(m,8H) ppm.

Example 7

Preparation of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl))iminooxymethyl]phenylacetic acid monomethylamide

2.8 g (5.0 mmol) of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl)iminooxymethyl]phenylacetate are dissolved in 10 ml of tetrahydrofuran, treated with 3.9 g of 40% strength aqueous monomethylamine solution and stirred at room temperature for 16 h. The mixture is then treated with water and extracted with methyl tert-butyl ether, and the organic phase is washed with water, dried over Na₂SO₄ and concentrated on a rotary evaporator. As a residue, 2.3 g (82%) of the title compound remain as a colorless oil.

¹H-NMR (CDCl₃):δ=1.08(s,9H); 1.26-1.41(m,4H); 1.53-1.67(m,4H); 1.89(s,3H); 2.56(t,2H); 2.87(d,3H); 3.93(s,3H); 3.99(t,2H); 5.02(s,2H); 6.74(s,broad,1H); 7.05-7.45(m,8H) ppm.

Example 8

Preparation of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″(1″′-methoxyimino, 1″′paramethoxyphenyl)methyl)iminooxymethyl]phenylacetic acid monomethylthioamide (Cpd. II.01, Table II)

1.9 g (4.5 mmol) of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″(1″′-methoxyimino, 1″′paramethoxyphenyl)methyl)iminooxy-methyl]phenylacetic acid monomethylamide are dissolved in 80 ml of xylene, treated with 1.8 g (4.5 mmol) of Lawesson's reagent and stirred at 100° C. for 45 min.

The reaction solution is concentrated and the residue is purified by column chromatography.

1.5 g (75%) of the title compound are isolated as an isomer mixture in the form of a yellowish oil.

IR [cm⁻¹] Film: 834, 977, 1027, 1065, 1175, 1251, 1358, 1512, 1608, 2936, 3330

Example 9

Isomerization of (E)-2-methoxyimono-2-[2′-(1″-methyl, 1″-(1″′-(Z/E)methoxyimino [sic], 1″′-phenyl)methyl)-(E)-iminooxymethyl]phenylacetic acid monomethylamide to (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(E)-methoxyimino [sic], 1″′-phenyl)methyl]-(E)-iminooxymethyl]phenylacetic acid monomethylamide:

5 g of E,E,E/E,Z,E isomer mixture (30:70) are dissolved in 50 ml of methanol, treated with 15 ml of methanol saturated with HCl and allowed to stand at room temperature for 18 hours. The reaction solution is added to ice-water and extracted with dichloromethane, and the extract is dried over Na₂SO₄. After concentrating on the rotary evaporator, 5 g of an oil (E,E,E:E,Z,E, approx. 65:35) are obtained. The desired (E,E,E)-isomer crystallizes on addition of methanol (2.1 g=42%) in the form of a colorless solid. M.p. (E,E,E-isomer): 134-136° C.

Note: The filtrate can be isomerized again using methanol HCl.

TABLE I

No. R² _(m) R³ R⁴ R⁵ Data I.01 H CH₃ CH₃ H m.p.: 135-138° C. I.02 H CH₃ CH₃ CH₃ m.p.: 78-82° C. I.03 H CH₃ CH₃ C₂H₅ oil; IR (Film): 3350, 2975, 2937, 1669, 1526, 1366, 1092, 1039, 980, 920, 890 I.04 H CH₃ CH₃ i-C₃H₇ oil; ¹H-NMR(CDCl₃)I: δ = 1.26(d, 6H); 1.95(s, 3H); 2.0(s, 3H) 2.91(d, 3H); 3.96(s, 3H); 4.37(q, 1H); 5.06(s, 2H), 6.72(s, br, 1H); 7.17-7.50(m, 4H) ppm I.05 H CH₃ CH₃ n-C₄H₉ m.p.: 89-93° C. I.06 H CH₃ CH₃ t-C₄H₉ oil; ¹H-NMR(CDCl₃): δ = 1.29(s, 9H); 1.94(s, 3H); 2.00(s, 3H); 2.90(d, 3H); 3.96(s, 3H); 5.06(s, 2H); 6.70(s, br, 1H); 7.17-747(m, 4H) ppm I.07 H CH₃ CH₃ n-C₆H₁₃ m.p.: 83-85° C. I.08 H CH₃ CH₃ CH₂CN m.p.: 92-96° C. I.09 H CH₃ CH₃ CH₂CH₂CN m.p.: 92-96° C. I.10 H CH₃ CH₃ 3-Methyl- m.p.: 86-88° C. but-2-en-1-yl I.11 H CH₃ CH₃ 4-Cl—C₆H₄—CH₂ m.p.: 152-154° C. I.12 H CH₃ CH₃ 2-Naphthyl-CH₂ oil; ¹H-NMR(CDCl₃): δ = 1.98(s, 3H); 2.02(s, 3H) 2.87(d, 3H); 3.92(s, 3H); 5.06(s, 2H); 5.33(s, 2H); 6.70(s, br, 1H); 7.17-7.88(m, 11H) ppm I.13 H CH₃ CH₃ 6-(4′-Chloro- oil; ¹H-NMR(CDCl₃): δ = phenyl)hex-1-yl 1.27-1.70(m, 8H); 1.95(s, 3H); 1.98(s, 3H); 2.58(t-2H); 2.90(d, 3H); 3.95(s, 3H); 4.10(t, 2H); 5.06(s, 2H); 6.71(s, br, 1H); 7.08-7.46(m, 8H) ppm I.14 H CH₃ CH₃ 3-CF₃—C₆H₄ m.p.: 119-124° C. I.15 H CH₃ CH₃ 4-CF₃, 6-Cl- m.p.: 129-132° C. pyrid-2-yl I.16 H CH₃ CH₃ 4-CF₃-pyrid-2-yl m.p.: 144-147° C. I.17 H CH₃ CH₃ (E)-1-Chloropropen- m.p.: 96-98° C. 3-yl I.18 H CH₃ CH₃ (E)-4-(4′- oil; ¹H-NMR(CDCl₃): Chlorophenyl)- 1.97(s, 6H); but-2-en-1-yl 2.90(d, 3H); 3.36(d, 2H); 3.96(s, 3H); 4.60(d, 2H); 5.06(s, 2H); 5.65-5.92(m, 2H); 7.68(s, br, 1H); 7.09-7.48(m, 8H) ppm I.19 H CH₃ CH₃ Propyn-3-yl m.p.: 106-109° C. I.20 H CH₃ CH₃ 2-Hydroxy- JR: 884, 929, 980, prop-1-yl 1036, 1092, 1366, 1529, 1665, 2937, 3370 I.21 H CH₃ CH₃ 6-Hydroxy-2- 217-220° C. methyl-pyrimidin- 4-ylmethyl I.22 H CH₃ CH₃ 6-Hydroxy-2-iso- 219-221° C. propyl-pyrimidin- 4-ylmethyl I.23 H CH₃ CH₃ 6-Hydroxy-2- 220-224° C. cyclopropyl- pyrimidin-4-ylmethyl I.24 H CH₃ CH₃ 5-(2′-Furan)- 57-61° C. pent-1-yl I.25 H CH₃ CH₃ 5-(2′-N-Methyl- 40-44° C. pyrrol)-pent-1-yl I.26 H CH₃ CH₃ 2-(4′-Chloro- 110-120° C. phenyl)-oxazol- 4-ylmethyl I.27 H CH₃ CH₃ 3-Trifluoro- 104-107° C. methylpyrid-2-yl I.28 H CH₃ CH₃ 5-Trifluoro- 126-130° C. methylpyrid-2-yl I.29 H CH₃ CH₃ 6-(2′-Thiophen)- 694, 893, 980, 1037, hex-1-yl 1092, 1365, 1525, 1673, 2935, 3340, 3400 I.30 H CH₃ t-C₄H₉ H oil; ¹H-NMR(CDCl₃): δ = 1.10(s, 9H); 1.95(s, 3H); 2.88(d, 3H); 3.95(s, 3H); 5.05(s, 2H); 6.76(s, br, 1H); 7.17-7.47(m, 4H); 8.04(s, 1H) ppm I.31 H CH₃ t-C₄H₉ CH₃ oil; IR (Film): 3360, 2963, 2936, 1671, 1525, 1364, 1091, 1041, 979, 887 I.32 H CH₃ t-C₄H₉ C₂H₅ oil; IR (Film): 3350, 2969, 2935, 1669, 1524, 1364, 1093, 1041, 978, 917, 883 I.33 H CH₃ t-C₄H₉ i-C₃H₇ m.p.: 95-99° C. I.34 H CH₃ t-C₄H₉ n-C₄H₉ oil; IR (Film): 3360, 2958, 2935, 2872, 1671, 1525, 1364, 1092, 1037, 979, 922 I.35 H CH₃ t-C₄H₉ t-C₄H₉ m.p.: 89-92° C. I.36 H CH₃ t-C₄H₉ n-C₆H₁₃ oil; IR (Film): 3360, 2956, 2933, 2870, 1675, 1525, 1364, 1093, 1039, 979, 918 I.37 H CH₃ t-C₄H₉ (E)-1-Chloro- oil; IR (Film): propen-3-yl 3360, 2966, 2935, 1673, 1526, 1365, 1093, 1037, 980, 918, 881 I.38 H CH₃ t-C₄H₉ Propyn-3-yl oil; IR (Film): 3300, 2967, 2935, 1672, 1525, 1365, 1094, 1037, 1005, 979, 918 I.39 H CH₃ t-C₄H₉ 3-Methyl- oil; IR (Film): but-2-en-1-yl 3360, 2968, 2935, 1675, 1525, 1364, 1093, 1038, 979, 919, 880 I.40 H CH₃ t-C₄H₉ 2-Naphthyl-CH₂ oil; IR (Film): 3360, 2966, 2935, 1675, 1523, 1364, 1037, 1002, 979, 920, 752 I.41 H CH₃ t-C₄H₉ 4-Cl—C₆H₄—CH₂ oil; IR (Film): 3360, 2970, 2945, 1677, 1525, 1492, 1365, 1090, 1038, 1014, 980, 919, 881 I.42 H CH₃ t-C₄H₉ (E)-4-(4′- oil; IR (Film): Chlorophenyl)- 3360, 2967, 1676, but-2-en-1-yl 1525, 1491, 1365, 1093, 1037, 1015, 979, 919 I.43 H CH₃ t-C₄H₉ 6-(4′-Chloro- oil; IR (Film): phenyl)hex-1-yl 3360, 2934, 1679, 1524, 1492, 1364, 1092, 1038, 1015, 979 I.44 H CH₃ t-C₄H₉ 3-CF₃—C₆H₄ oil; IR (Film): 3360, 2975, 1675, 1450, 1331, 1168, 1126, 1092, 1038, 980, 940, 926 I.45 H CH₃ C₆H₅ H m.p.: 165-167° C. I.46 H CH₃ C₆H₅ CH₃ m.p.: 134-136° C. I.47 H CH₃ C₆H₅ C₂H₅ oil; IR (Film): 3340, 2938, 1674, 1526, 1445, 1091, 1037, 979, 925, 767, 694 I.48 H CH₃ C₆H₅ i-C₃H₇ m.p.: 77-80° C. I.49 H CH₃ C₆H₅ n-C₄H₉ oil; IR (Film): 3340, 2958, 2936, 1675, 1525, 1445, 1092, 1070, 1036, 979, 694 I.50 H CH₃ C₆H₅ 4-Cl—C₆H₄—CH₂ oil; IR (Film): 3340, 2937, 1675, 1522, 1492, 1445, 1091, 1036, 1012, 979, 918 I.51 H CH₃ C₆H₅ 3-CF₃—C₆H₄ oil; IR (Film): 3340, 2930, 1675, 1449, 1328, 1169, 1126, 1062, 1038, 979, 944, 697 I.52 H CH₃ C₆H₅ 6-(4′-Chloro- oil; IR (Film): phenyl)hex-1-yl 3340, 2935, 2858, 1679, 1524, 1492, 1445, 1091, 1037, 1015, 979 I.53 H CH₃ C₆H₅ (E)-4-(4′- oil; IR (Film): Chlorophenyl)- 3340, 2937, 1675, but-2-en-1-yl 1525, 1491, 1444, 1092, 1036, 1015, 978, 918 I.54 H C₆H₅ C₆H₅ CH₃ m.p.: 60-65° C. I.55 H C₆H₅ C₆H₅ C₂H₅ m.p.: 45-48° C. I.56 H C₆H₅ C₆H₅ n-C₃H₇ oil, IR [cm⁻¹] (Film) 693, 766, 980, 1037, 1064, 1445, 1526, 1676, 2937, 2965, 3330, 3410 I.57 H C₆H₅ C₆H₅ i-C₃H₇ m.p. 53-58° C. I.58 H C₆H₅ C₆H₅ n-C₄H₉ oil, IR [cm⁻¹] (Film) 693, 766, 978, 1015, 1036, 1445, 1525, 1677, 2936, 2958, 3340, 3420 I.59 H C₆H₅ C₆H₅ t-C₄H₉ m.p.: 45-50° C. I.60 H C₆H₅ C₆H₅ n-C₆H₁₃ oil, IR [cm⁻¹] (Film) 693, 766, 979, 1014, 1037, 1445, 1525, 1678, 2934, 2954, 3330, 3410 I.61 H C₆H₅ C₆H₅ 3-Methyl- oil, IR [cm⁻¹] (Film) but-2-en-1-yl 693, 766, 921, 979, 1037, 1445, 1493, 1526, 1675, 2937, 3330, 3410 I.62 H CH₃ CH₃ 4-Phenyl- oil, IR [cm⁻¹] (Film) but-1-yl 700, 748, 894, 923, 979, 1037, 1365, 1524, 1673, 2938, 3340, 3410 I.63 H CH₃ CH₃ 4-Phenoxy- oil, IR [cm⁻¹] (Film) but-1-yl 755, 891, 980, 1037, 1245, 1498, 1525, 1600, 1674, 2939, 3350, 3410 I.64 H CH₃ CH₃ 2-(2′-Fluoro- oil, IR [cm⁻¹] (Film) phenoxy)eth-1-yl 749, 889, 924, 979, 1037, 1260, 1366, 1507, 1524, 1673, 2930, 3340, 3410 I.65 H CH₃ CH₃ 3-(2′-Fluoro- oil, IR [cm⁻¹] (Film) phenoxy)-prop-1- 749, 979, 1037, yl 1204, 1260, 1280, 1366, 1507, 1524, 1675, 2930, 3340, 3420 I.66 H CH₃ CH₃ E-4-(2′-Fluoro- oil, IR [cm⁻¹] (Film) phenoxy)-but-1- 749, 891, 980, 1037, yl 1205, 1259, 1366, 1507, 1524, 1675, 2930, 3340, 3420 I.67 H CH₃ CH₃ 6-(4′-Chloro- m.p.: 58-62° C. phenoxy)-hex-1- yl I.68 H CH₃ CH₃ 2-(4′-Chloro- oil, IR (cm⁻¹] (Film) phenoxy)-prop-1- 885, 979, 1007, 1037, yl 1091, 1241, 1366, 1490, 1525, 1674, 2930, 3340, 3420 I.69 H CH₃ CH₃ C₆H₅—C₂H₄—O—C₂H₄— oil, IR [cm⁻¹] (Film) 893, 920, 979, 1038, 1092, 1124, 1365, 1524, 1674, 2937, 3350, 3420 I.70 H CH₃ CH₃ E-4-(3′-Methoxy- oil, IR [cm⁻¹] (Film) phenyl)-but-3- 890, 978, 1038, 1156, en-1-yl 1365, 1525, 1579, 1598, 1675, 2937, 3320, 3390 I.71 H CH₃ CH₃ E-4-(4′-Fluoro- m.p.: 77-81° C. phenyl)-but-3- en-1-yl I.72 H CH₃ CH₃ (3-Bromoisoxazol- IR [cm⁻¹] (Film) 5-yl)-methyl 769, 889, 904, 951, 988, 1001, 1035, 1359, 1526, 1677, 3420 I.73 H CH₃ CH₃ (3-CF₃-isoxazol- IR [cm⁻¹] (KBr) 5-yl)-methyl 769, 893, 987, 999, 1034, 1150, 1192, 1221, 1674, 3430 I.74 H CH₃ CH₃ (3-iso-Propyl- oil, IR [cm⁻¹] (Film) isoxazol-5-yl)- 883, 900, 980, 1000, methyl 1036, 1366, 1525, 1673, 2937, 2968, 3340 I.75 H CH₃ CH₃ (3-Cyclopropyl- oil, IR [cm⁻¹] (Film) isoxazol-5-yl)- 883, 907, 980, 1000, methyl 1036, 1366, 1434, 1526, 1608, 1673, 2930, 3340 I.76 H CH₃ CH₃ (3-iso-Propyl- oil, IR [cm⁻¹] (Film) 1,2,4-Oxadiazol- 882, 979, 1019, 1037, 5-yl)-methyl 1091, 1366, 1525, 1674, 2938, 2972, 3340 I.77 H CH₃ CH₃

m.p.: 160-165° C. I.78 H CH₃ 4-OCH₃—C₆H₄ CH₃ m.p.: 121-125° C. I.79 H CH₃ 4-OCH₃—C₆H₄ C₂H₅ oil, IR [cm⁻¹] (Film) 922, 979, 1036, 1091, 1176, 1252, 1512, 1608, 1675, 2937, 3340 I.80 H CH₃ 4-OCH₃—C₆H₄ n-C₃H₇ oil, IR [cm⁻¹] (Film) 979, 1037, 1067, 1176, 1252, 1512, 1608, 1676, 2936, 2965, 3350 I.81 H CH₃ 4-OCH₃—C₆H₄ i-C₃H₇ oil, IR [cm⁻¹] (Film) 977, 1037, 1122, 1174, 1252, 1512, 1608, 1676, 2937, 2974, 3340 I.82 H CH₃ 4-OCH₃—C₆H₄ n-C₄H₉ oil, IR [cm⁻¹] (Film) 835, 978, 1035, 1176, 1252, 1512, 1608, 1675, 2936, 2958, 3340 I.83 H CH₃ 4-OCH₃—C₆H₄ t-C₄H₉ IR [cm⁻¹] (Film) 958, 979, 1036, 1174, 1191, 1253, 1364, 1513, 1609, 1678, 2930, 2970, 3420 I.84 H CH₃ C₆H₅

m.p.: 120-124° C. I.85 H CH₃ C₆H₅ 3-Fluorobenzyl oil, IR [cm⁻¹] (Film) 695, 919, 979, 1002, 1036, 1447, 1488, 1525, 1591, 1676, 2920, 3330, 3410 I.86 H CH₃ C₆H₅ 3-Bromobenzyl oil, IR [cm⁻¹] (Film) 696, 776, 979, 1002, 1036, 1069, 1092, 1445, 1524, 1676, 2920, 3330, 3400 I.87 H CH₃ C₆H₅ 3-CF₃-Benzyl oil, IR [cm⁻¹] (Film) 979, 1003, 1036, 1074, 1125, 1166, 1201, 1330, 1525, 1676, 2920, 3330 I.88 H CH₃ C₆H₅ 4-Chlorophenyl m.p. 58-62° C. I.89 H CH₃ C₆H₅ 3,4-Dichloro- oil, IR [cm⁻¹] (Film) benzyl 693, 880, 919, 979, 1002, 1035, 1445, 1471, 1525, 1676, 2930, 3340, 3420 I.90 H CH₃ CH₃ 2-Methoxy- oil; IR [cm⁻¹] (Film) eth-1-yl 891, 919, 980, 1038, 1093, 1127, 1366, 1525, 1673, 2870, 2937, 3340 I.91 H CH₃ 4-Cl—C₆H₄ CH₃ oil; IR [cm⁻¹] (Film) 875, 894, 979, 1012, 1037, 1091, 1491, 1525, 1674, 2890, 2938, 3340 I.92 H CH₃ 4-Cl—C₆H₄ C₂H₅ oil; IR [cm⁻¹] (Film) 924, 979, 1012, 1037, 1091, 1491, 1526, 1673, 2938, 2976, 3340 I.93 H CH₃ 4-Cl—C₆H₄ n-C₃H₇ oil; IR [cm⁻¹] (Film) 979, 1012, 1038, 1067, 1092, 1491, 1525, 1675, 2937, 2967, 3340 I.94 H CH₃ 4-Cl—C₆H₄ i-C₃H₇ oil; IR [cm⁻¹] (Film) 977, 1016, 1038, 1091, 1121, 1370, 1490, 1525, 1675, 2930, 2975, 3340 I.95 H CH₃ 4-Cl—C₆H₄ n-C₄H₉ oil; IR [cm⁻¹] (Film) 979, 1012, 1037, 1070, 1091, 1491, 1525, 1674, 2936, 2959, 3330 I.96 H CH₃ 4-Cl—C₆H₄ t-C₄H₉ m.p.: 67-71° C. I.97 H CH₃ 4-Cl—C₆H₄ n-C₆H₁₃ oil; IR [cm⁻¹] (Film) 979, 1011, 1038, 1091, 1491, 1525, 1675, 2872, 2934, 2954, 3330 I.98 H CH₃ 4-Cl—C₆H₄ 3-Methyl- oil; IR [cm⁻¹] (Film) but-2-en-1-yl 833, 878, 979, 1038, 1091, 1447, 1491, 1525, 1675, 2937, 3330 I.99 H CH₃ 4-Cl—C₆H₄ Propargyl m.p.: 109-114° C. I.100 H CH₃ 4-F—C₆H₄ CH₃ m.p.: 130-132° C. I.101 H CH₃ 4-F—C₆H₄ C₂H₅ m.p.: 105-110° C. I.102 H CH₃ 4-F—C₆H₄ n-C₃H₇ oil; IR [cm⁻¹] (Film) 840, 979, 1038, 1223, 1508, 1523, 1605, 1673, 2937, 2967, 3360 I.103 H CH₃ 4-F—C₆H₄ i-C₃H₇ oil; IR [cm⁻¹] (Film) 840, 978, 1038, 1122, 1158, 1224, 1509, 1525, 1675, 2930, 2975, 3340 I.104 H CH₃ 4-F—C₆H₄ t-C₄H₉ m.p.: 95-100° C. I.105 H CH₃ 4-F—C₆H₄ n-C₄H₉ oil; IR [cm⁻¹] (Film) 840, 979, 1013, 1037, 1224 1509, 1524, 1675 2936, 2959, 3340 I.106 H CH₃ 4-F—C₆H₄ n-C₆H₁₃ oil; IR [cm⁻¹] (Film) 840, 979, 1011, 1038, 1225, 1509, 1524, 1605, 1676, 2935, 3340 I.107 H CH₃ 4-F—C₆H₄ 3-Methyl- oil; IR [cm⁻¹] (Film) but-2-en-1-yl 841, 980, 1038, 1159, 1224, 1509, 1525, 1605, 1675, 2938, 3350 I.108 H CH₃ 4-F—C₆H₄ Propargyl oil; IR [cm⁻¹] (Film) 841, 875, 980, 1005, 1035, 1222, 1509, 1525, 1602, 1674, 2110, 2930, 3250, 3340 I.109 H CH₃ 4-Cl—C₆H₄ 3-iso-Propyl- oil; IR [cm⁻¹] (Film) 1,2,4-oxadiazol- 874, 980, 1011, 1038, 5-yl)-methyl 1092, 1491, 1525, 1588, 1676, 2940, 2973, 3350 I.110 H CH₃ 4-Cl—C₆H₄ Thiazol-4-yl- m.p.: 46-48° C. methyl I.111 H CH₃ 4-Cl—C₆H₄ (3-iso-Propyl- oil; IR [cm⁻¹] (Film) isoxazol- 981, 999, 1013, 1036, 5-yl)-methyl 1092, 1491, 1526, 1675, 2938, 2968, 3340 I.112 H CH₃ 4-Cl—C₆H₄ (3-Bromo-isoxazol- m.p.: 46-49° C. 5-yl)-methyl I.113 H CH₃ 4-Cl—C₆H₄ (3-CF₃-isoxazol- oil; IR [cm⁻¹] (Film) 5-yl)-methyl 970, 980, 999, 1013, 1036, 1092, 1155, 1190, 1491, 1671, 2940, 3340 I.114 H CH₃ 3-Cl—C₆H₄ CH₃ m.p.: 117-120° C. I.115 H CH₃ C₂H₅ CH₃ m.p.: 74-77° C. I.116 H CH₃ C₂H₅ C₂H₅ oil; IR [cm⁻¹] (Film) 768, 926, 960, 975, 1021, 1041, 1053, 1654, 1671, 2970, 3296 I.117 H CH₃ 4-CH₃—C₆H₄ CH₃ oil; IR [cm⁻¹] (Film) 980, 1006, 1037, 1092, 1447, 1461, 1528, 1669, 2939, 3349 I.118 H CH₃ 4-CH₃—C₆H₄ C₂H₅ oil; IR [cm⁻¹] (Film) 923, 954, 980, 1037, 1091, 1447, 1528, 1669, 2938, 2976, 3340 I.119 H CH₃ 4-CH₃—C₆H₄ n-C₃H₇ oil; IR [cm⁻¹] (Film) 911, 979, 1039, 1067, 1092, 1458, 1525, 1673, 2936, 2965, 3340 I.120 H CH₃ 3-Cl—C₆H₄ C₂H₅ oil; IR [cm⁻¹] (Film) 924, 979, 1012, 1037, 1091, 1411, 1525, 1673, 2937, 2976, 3350 I.121 H CH₃ 3-Cl—C₆H₄ n-C₃H₇ oil; IR [cm⁻¹] (Film) 917, 980, 1038, 1067, 1093, 1411, 1525, 1673, 2937, 2966, 3340 I.122 H CH₃ 3-Cl—C₆H₄ i-C₃H₇ oil; IR [cm⁻¹] (Film) 979, 1038, 1093, 1121, 1370, 1412, 1526, 1673, 2937, 2975, 3340 I.123 H CH₃ 3-Cl—C₆H₄ n-C₄H₉ oil; IR [cm⁻¹] (Film) 882, 979, 1037, 1071, 1092, 1412, 1525, 1674, 2936, 2959, 3350 I.124 H CH₃ 3-Cl—C₆H₄ 3-Chloro- oil; IR [cm⁻¹] (Film) prop-2-en-1-yl 789, 880, 932, 960, 1006, 1037, 1092, 1412, 1525, 1675, 2930, 3420 I.125 H CH₃ 3-Cl—C₆H₄ Propargyl oil; IR [cm⁻¹] (Film) 695, 885, 927, 980, 1006, 1035, 1092, 1412, 1525, 1674, 2110, 2930, 3290 I.126 H CH₃ 2-Cl—C₆H₄ CH₃ m.p.: 160-162° C. I.127 H CH₃ 2-Cl—C₆H₄ C₂H₅ m.p.: 125-127° C. I.128 H CH₃ 2-Cl—C₆H₄ n-C₃H₇ m.p.: 102-103° C. I.129 H CH₃ 3-CH₃-isoxazol- CH₃ oil; IR [cm⁻¹] (Film) 5-yl 3345 2940, 1675, 1526, 1446, 1412, 1068, 1038, 979, 959, 897 I.130 H CH₃ 3-CH₃-isoxazol- C₂H₅ oil; IR [cm⁻¹] (Film) 5-yl 3340, 2939, 1675, 1526, 1446, 1412, 1091, 1037, 980, 957, 921 I.131 H CH₃ 3-CH₃-isoxazol- n-C₃H₇ oil; IR [cm⁻¹] (Film) 5-yl 3350, 2938, 1675, 1526, 1447, 1412, 1068, 1037, 1011, 980, 960 I.132 H CH₃ 3-CH₃-isoxazol- i-C₃H₇ oil; IR [cm⁻¹] (Film) 5-yl 3345, 2977, 2938, 1675, 1527, 1412, 1371, 1119, 1037, 982, 949 I.133 H CH₃ 3-CH₃-isoxazol- n-C₄H₉ oil; IR [cm⁻¹] (Film) 5-yl 3340, 2959, 2937, 1676, 1526, 1447, 1412, 1071, 1036, 980, 951 I.134 H CH₃ 3-CH₃-isoxazol- n-C₆H₁₃ oil; IR [cm⁻¹] (Film) 5-yl 3340, 2935, 1676, 1526, 1447, 1412, 1092, 1037, 1016, 980, 958 I.135 H CH₃ 3-CH₃-isoxazol- Prop-1-en-3-yl oil; IR [cm⁻¹] (Film) 5-yl 3345, 2935, 1675, 1527, 1446, 1413, 1092, 1036, 1014, 981, 942, 919 I.136 H CH₃ 3-CH₃-isoxazol- (E)-1-Chloro- oil; IR [cm⁻¹] (Film) 5-yl prop-1-en-3-yl 3340, 2938, 1674, 1527, 1446, 1412, 1092, 1036, 1014, 981, 949 I.137 Cl CH₃ CH₃ CH₃ m.p.: 120-122° C. I.138 Cl CH₃ C₆H₅ CH₃ m.p.: 190-192° C. I.139 Cl CH₃ C₆H₅ C₂H₅ oil; IR [cm⁻¹] (Film) 1039, 1444, 1528, 1676, 2038, 3350 I.140 H SCH₃ CH₃ CH₃ oil; IR [cm⁻¹] (Film) 3340, 1671, 1526, 1094, 1074, 1039, 1014, 980, 957, 877 I.141 H SCH₃ CH₃ C₂H₅ oil; IR [cm⁻¹] (Film) 3335, 2936, 1672, 1526, 1442, 1411, 1365, 1092, 1039, 981, 884 I.142 H SCH₃ CH₃ n-C₃H₇ oil; IR [cm⁻¹] (Film) 3340, 2965, 2936, 1672, 1526, 1365, 1094, 1064, 1037, 981, 960 I.143 H SCH₃ CH₃ i-C₃H₇ oil; IR [cm⁻¹] (Film) 3340, 2958, 2935, 2871, 1672, 1526, 1436, 1365, 1093, 1037, 980 I.144 H SCH₃ CH₃ n-C₆H₁₃ oil; IR [cm⁻¹] (Film) 3340, 2954, 2933, 2871, 1672, 1526, 1436, 1365, 1093, 1037, 980 I.145 H SCH₃ CH₃ Prop-1-en-3-yl oil; IR [cm⁻¹] (Film) 3340, 2935, 1672, 1526, 1412, 1094, 1036, 980, 959, 923, 871 I.146 H SCH₃ CH₃ 3-CF₃—C₆H₄—CH₂ oil; IR [cm⁻¹] (Film) 3340, 2930, 1673, 1528, 1330, 1165, 1125, 1098, 1074, 1038, 982 I.147 H CH₃ 3-Pyridyl CH₃ oil; IR [cm⁻¹] (Film) 3340, 2939, 1672, 1526, 1412, 1071, 1038, 1005, 979, 896, 873

TABLE II

No. R² _(m) R³ R⁴ R⁵ Data II.01 H CH₃ p-OCH₃—C₆H₄ CH₃ oil, IR [cm⁻¹] (Film) 834, 977, 1027, 1065, 1175, 1251, 1358, 1512, 1175, 1608, 2936, 3330 II.02 H CH₃ p-OCH₃—C₆H₄ n-C₃H₇ oil, IR [cm⁻¹] (Film) 977, 1027, 1066, 1176, 1251, 1358, 1512, 1607, 2935, 2964, 3340 II.03 H CH₃ p-OCH₃—C₆H₄ n-C₄H₉ oil, IR [cm⁻¹] (Film) 834, 975, 1027, 1175, 1252, 1359, 1512, 1607, 2934, 2957, 3340 II.04 H CH₃ C₆H₅ 3-Fluoro- m.p. 142-150° C. benzyl II.05 H CH₃ C₆H₅ 3-CF₃-benzyl oil, IR [cm⁻¹] (Film) 701, 1027, 1073, 1100, 1125, 1166, 1201, 1329, 1361, 1519, 2920, 3340 II.06 H CH₃ C₆H₅ 3,4-Dichloro- oil, IR [cm⁻¹] (Film) benzyl 694, 769, 877, 893, 975, 1028, 1357, 1471, 1519, 2935, 3340 II.07 H CH₃ C₆H₅ 4-Chloro- m.p. 55-60° C. phenyl II.08 H CH₃ C₆H₅ 3-Bromobenzyl oil, IR [cm⁻¹] (Film) 696, 773, 876, 893, 975, 1028, 1064, 1358, 1519, 2935, 3350 II.09 H CH₃ 4-Cl—C₆H₄ i-C₃H₇ oil, IR [cm⁻¹] (Film) 942, 974, 1027, 1091, 1121, 1358, 1369, 1490, 1518, 2920, 2975, 3350 II.10 H CH₃ 4-Cl—C₆H₄ n-C₄H₉ oil, IR [cm⁻¹] (Film) 830, 976, 1027, 1091, 1358, 1490, 1518, 2934, 2958, 3350 II.11 H CH₃ 4-Cl—C₆H₄ t-C₄H₉ oil, IR [cm⁻¹] (Film) 894, 973, 1030, 1089, 1188, 1364, 1490, 1519, 2934, 2977, 3350 II.12 H CH₃ 4-Cl—C₆H₄ n-C₆H₁₃ oil, IR [cm⁻¹] (Film) 830, 977, 1027, 1091, 1357, 1490, 1518, 2871, 2932, 2954, 3350 II.13 H CH₃ 4-F—C₆H₄ C₂H₅ oil, IR [cm⁻¹] (Film) 841, 976, 1027, 1058, 1225, 1358, 1509, 2936, 2970, 3360 II.14 H CH₃ 4-F—C₆H₄ n-C₃H₇ oil, IR [cm⁻¹] (Film) 840, 978, 1027, 1065, 1225, 1359, 1508, 1604, 2936, 2966, 3360 II.15 H CH₃ 4-F—C₆H₄ t-C₄H₉ m.p.: 113-119° C.

Examples of the action against harmful fungi;

It was possible to show the fungicidal action of the compounds of the general formula I by the following tests:

The active compounds were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and correspondingly diluted to the desired concentration with water.

1. Erysiphe graminis var. tritici

Leaves of wheat seedlings (Kanzler variety) were first treated with the aqueous preparation of the active compounds (containing 250 ppm). After about 24 h, the plants were dusted with spores of powdery mildew of wheat (Erysiphe graminis var. tritici). The plants treated in this way were then incubated for 7 days at 20-22° C. and a relative atmospheric humidity of 75-80%. The extent of fungal development was then determined.

In this test, the plants treated with the compounds according to the invention showed an attack of 5% or less, the plants treated with a known active compound (compound No. 195, Table 3, EP-A 463 488) showed 25% attack and the untreated plants showed 70% attack.

In a corresponding test (wheat seedlings of the Kanzler variety, application rate 250 ppm), the plants were first infected and incubated and then treated with the active compounds. In this test, the plants treated with the compounds according to the invention showed an attack of 5% or less and the untreated plants showed 60% attack.

Examples of the action against animal pests:

It was possible to show the insecticidal action of the compounds of the general formula I by the following tests:

The active compounds were prepared

a) as a 0.1% strength solution in acetone or

b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanol, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor®EL (Emluan®EL, emulsifier based on ethoxylated fatty alcohols)

and correspondingly diluted to the desired concentration with acetone in the case of a) or with water in the case of b).

After termination of the tests, in each case the lowest concentration was determined at which the compounds still caused an 80-100% inhibition or mortality in comparison to untreated control tests (action threshold or minimum concentration).

Aphis fabae (black fly), contact action

Heavily infested dwarf beans (Vicia faba) were treated with the aqueous active compound preparation. The mortality rate was determined after 24 h.

In this test, the compounds I.68, I.69, I.70, I.71, I.81, I.86, I.94, I.97, I.103, I.105, I.106, II.12 and II.13 according to the invention showed action thresholds of 400 ppm or less.

Nephotettix cincticeps (green rice leaf hopper), contact action

Circular filters were treated with the aqueous active compound preparation and then occupied by 5 adult leaf hoppers. The mortality was assessed after 24 h.

In this test, the compounds I.02, I.04, I.10, I.17, I.24, I.29, I.46, I.47, I.48, I.52, I.55, I.74, I.75, I.78, I.79 and I.92 according to the invention showed action thresholds of 0.4 mg or less.

Prodenia litura (Egyptian cotton leaf worm), contact action

Filters treated with the aqueous active compound preparation were occupied by 5 caterpillars. The first assessment is carried out after 4 h. If at least one caterpillar is still living, a feed mixture is added. The mortality was determined after 24 h.

In this test, the compounds I.04, I.17, I.78, I.79, I.91, I.92, I.94, I.101, I.102, I.103 and I.108 according to the invention showed action thresholds of 0.4 mg or less.

Tetranychus telarius (common red spider mite), contact action

Potted dwarf beans having the second successive pair of leaves were treated with aqueous active compound preparation. After 24 h, the plants were infected using heavily infested pieces of leaf. The attack was determined after 12 days in the greenhouse.

In this test, the compounds I.37, I.91, I.92, I.93, I.97, I.101, I.102, I.104, I.105, I.106, I.108, II.13, II.14 and II.15 showed action thresholds of 400 ppm or less. 

We claim:
 1. A phenylacetic acid compound of the formula I

where the substituents and the index have the following meanings: X is oxygen or sulfur; R is hydrogen and or C₁-C₄-alkyl; R¹ is hydrogen and C₁-C₄-alkyl; R² is cyano, nitro, trifluoromethyl, halogen, C₁-C₄-alkyl and or C₁-C₄-alkoxy; m is 0, 1 or 2, it being possible for the R² radicals to be different if m is 2; R³ is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino or di-C₁-C₄-alkylamino; R⁴ is C₁-C₆-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C₁-C₄-alkoxy, arylthio, aryl-C₁-C₄-alkylthio, hetaryl, hetaryloxy, hetaryl-C₁-C₄-alkoxy, hetarylthio, hetaryl-C₁-C₄-alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR⁶)—A_(n)—R⁷; or C₃-C₆-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R⁵ is hydrogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR⁶)—A_(n)—R⁷; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR⁶)—A_(n)—R⁷; A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C₁-C₆-alkyl; n is 0 or 1; R⁶ is hydrogen or C₁-C₆-alkyl and R⁷ is hydrogen or C₁-C₆-alkyl, or a salt thereof.
 2. The compound of the formula I defined in claim 1, wherein R³ is hydrogen, hydroxyl, cyclopropyl, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio, and R⁵ is hydrogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR⁶)—A_(n)—R⁷; or aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR⁶)—A_(n)—R⁷; or a salt thereof.
 3. The compound of the formula I defined in claim 1, wherein m is
 0. 4. The A compound of the formula I defined in claim 1, wherein R¹ is methyl.
 5. The compound defined in claim 1, wherein R⁴ denotes C₁-C₆-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, hydroxyl, halogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, heterocyclyl, aryl, aryloxy, hetaryl and hetaryloxy, or C₃-C₆-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy.
 6. The compound defined in claim 1, wherein R⁴ denotes C₁-C₆-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: halogen and C₁-C₆-alkoxy.
 7. A process for preparing a compound of the formula I as defined in claim 1, wherein R³ is not halogen, which comprises reacting a benzyl compound of the formula II

wherein L¹ is a nucleophilically replaceable leaving group, with a hydroxyimine of the formula III R⁵ON═C(R⁴)—C(R³)═NOH   (III).
 8. A process for preparing a compound of the formula I as defined in claim 1, wherein R³ is not halogen, which comprises reacting a benzyl compound of the formula II

with a dihydroxyimine of the formula IV HON═C(R⁴)—C(R³)═NOH   (IV) to give a compound of the formula V

and then reacting V with a compound of the formula VI R⁵—L²   (VI) wherein L² is a nucleophilically replaceable leaving group, to give I.
 9. A process for preparing a compound of the formula I defined in claim 1, wherein R³ is not halogen, which comprises reacting a benzyl compound of the formula II

with a carbonylhydroxyimine of the formula VII O═C(R⁴)—C(R³)═NOH   (VII) to give a compound of the formula VIII

then either reacting VIII a) first with hydroxylamine or its salt and then with a compound of the formula VI R⁵—L²   (VI) or b) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb R⁵ONH₂   (IXa) R⁵ONH₃ ^(⊕)Q^(⊖)  (IXb) where Q^(⊖) is the anion of an acid, to give I.
 10. A composition against animal pests or harmful fungi, comprising customary additives and an effective amount of a compound of the formula I defined in claim
 1. 11. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environment or the plants, surfaces, materials or spaces to be kept free from said pests or fungi with an effective amount of a compound of the formula I defined in claim
 1. 